N-Boc-beta-(2-thienyl)-DL-alanine → (RS)-alpha-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(thiophen-2-yl)propionamide

HRID 275620

Reaction equation

HRID 275620 reaction equation
C(OC([NH:8][CH:9]([CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[C:10]([OH:12])=O)=O)(C)(C)C.[NH2:19][C@@H:20]([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C@@H:21]([OH:27])[C@H:22]([CH:24]1[CH2:26][CH2:25]1)[OH:23]>>[NH2:8][CH:9]([CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[C:10]([NH:19][C@@H:20]([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C@@H:21]([OH:27])[C@H:22]([CH:24]1[CH2:26][CH2:25]1)[OH:23])=[O:12]

Participants

3

Reactant 2

HCID 5035100N-Boc-beta-(2-thienyl)-DL-alanineHCID 14930738(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol

Product 1

HCID 57152908(RS)-alpha-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(thiophen-2-yl)propionamide

Procedure

In an analogous manner to that described above, by the condensation of rac-α-(tert-butoxyformamido)-3-(thiophen-2-yl)propionic acid [Pol. J. Chem. 54(11-12), 2225 (1980)] and (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol followed by acidic hydrolysis there was obtained (RS)-α-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(thiophen-2-yl)propionamide, MS: 381 (M+H)+ as a colourless foam.

Workup

  1. customfollowed by acidic hydrolysis there

Sources & evidence

ORD record
ord-3440aedb76e14389b64ed709460c5ea7
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Linked notes

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