Synthesis of ADBICA (ADB-PICA)

WillD

Expert
Joined
Jul 19, 2021
Messages
645
Reaction score
894
Points
93
1-Pentyl-3-(trifluoroacetyl)indole.
97Yx8oZ20y

1. A cooled (0 *C) suspension of NaH (60% dispersion in mineral oil, 68 g) in DMF (1000 ml) was treated with a solution of indole (100 g) in DMF (200 ml).
2. Warmed to rt, and stirred for 10 min.
3. The mixture was cooled to 0*C, treated slowly with the appropriate 1-bromopentane (135 g), warmed to rt, and stirred for 1 h.
4. The solution was cooled to 0 *C, treated with (CF3CO)2O (300 ml), warmed to rt, and stirred for 1 h.
5. The mixture was poured onto ice−water (6000 ml) and stirred vigorously.
6. The mixture was filtered, and the precipitate was dried to give the crude product as a red solid, which was used in the following step without purification, yield 100%.


1-Pentylindole-3-carboxylic Acid.
8Df4SWAvRo

1. To a refluxing solution of KOH (66 g) in MeOH (120 ml) was added, portionwise, a solution of the appropriate crude 1-pentyl-3-trifluoroacetylindole (100 g) in toluene (300 ml).
2. After heating at reflux for 2 h, the mixture was cooled to ambient temperature, and H2O (1000 ml) was added
3. The layers were separated, and the organic layer was extracted with 1M aq. NaOH (350 ml).
4. The combined aqueous phases were acidified to pH 1 with 10M aq. HCl, extracted with Et2O (3x500 ml), and dried (MgSO4), and the solvent was removed under reduced pressure.
5. The crude solid was recrystallized from i-PrOH to give the appropriate 37 g 1-pentylindole-3-carboxylic acid as colorless crystals.


ADBICA (S)-N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indole-3-carboxamide).
PmBdGr7yY1

1. A solution of the 1-Pentylindole-3-carboxylic Acid (100 g) in DMF (1000 ml) was treated with EDC (83 g), HOBt (59 g), DIPEA (190 g), L-tert-leucinamide (86 g) and stirred for 24 h.
2. The mixture was partitioned between and H2O (2000 ml) and EtOAc (1000 ml), the layers were separated, and the aqueous layer was extracted with EtOAc (2x500 ml).
3. The combined organic phases were dried (MgSO4), and the solvent was evaporated under reduced pressure.
4. The crude products were purified by recrystallization to get 112 g (75%) of a white solid.
 
Last edited by a moderator:

archae

Don't buy from me
Resident
Joined
Jan 25, 2022
Messages
77
Reaction score
62
Points
18
Just to be sure, is EDC 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide? CAS-1892-57-5? My other question is, as I have never worked with this compound, can the hydrochloride be used? AFAIC, they should have pretty similar solubility and acticity.
 

archae

Don't buy from me
Resident
Joined
Jan 25, 2022
Messages
77
Reaction score
62
Points
18
Just to be sure, is EDC 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide? CAS-1892-57-5? My other question is, as I have never worked with this compound, can the hydrochloride be used? AFAIC, they should have pretty similar solubility and acticity.
archaeNevermind, I'm pretty sure it is rather 1,2 dichloroethane :/
 

G.Patton

Expert
Joined
Jul 5, 2021
Messages
2,404
Solutions
3
Reaction score
2,365
Points
113
Deals
1
Just to be sure, is EDC 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide? CAS-1892-57-5? My other question is, as I have never worked with this compound, can the hydrochloride be used? AFAIC, they should have pretty similar solubility and acticity.
archaeYes, it is 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide. Sorry for a long reply.
My other question is, as I have never worked with this compound, can the hydrochloride be used? AFAIC, they should have pretty similar solubility and acticity.
I think yes.
 
  • Free product samples

    Testing products from new vendors and manufacturers.

    Get free samples for testing now!

  • Always stay in touch with BB forum. Element/Matrix.

    Connect notifications to always stay in touch with the forum!

    Connect

  • The BB Forum team is looking for cooperation:

    • Traffic arbitrage specialists
    • Spammers
    • Advertising agencies
    • Bloggers/Vloggers
    • TOR sites directories
    • Creative people who can create viral content
    • Administrators of Telegram Channels and Groups

      We will pay more for your traffic than our competitors! $0.1 per visitor!!!If you are interested in, write to the administrator.
Top