2-((tert-Butoxycarbonyl)amino)-3-(thiazol-4-yl)propanoic acid → tert-butyl [(RS)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-(4-thiazolyl)ethyl]carbamate

HRID 2294710Notes

Reaction equation

HRID 2294710 reaction equation
[C:1]([NH:8][CH:9]([C:16]([OH:18])=O)[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:19][CH:20]([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH:21]([OH:27])[CH:22]([CH:24]1[CH2:26][CH2:25]1)[OH:23]>>[CH:29]1([CH2:28][C@H:20]([NH:19][C:16]([CH:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:10][C:11]2[N:12]=[CH:13][S:14][CH:15]=2)=[O:18])[C@@H:21]([OH:27])[C@H:22]([CH:24]2[CH2:25][CH2:26]2)[OH:23])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

3

Reactant 2

HCID 145403222-((tert-Butoxycarbonyl)amino)-3-(thiazol-4-yl)propanoic acidHCID 18922883HCID 18922883, compound

Product 1

HCID 86751646tert-butyl [(RS)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-(4-thiazolyl)ethyl]carbamate

Procedure

In a manner analogous to the procedure described in Example 16(c), by condensing (RS)-Boc-3-(4-thiazolyl)alanine, prepared according to the synthesis described in EPA 0274259, and 3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol there is obtained tert-butyl [(RS)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-(4-thiazolyl)ethyl]carbamate (1:1 epimer mixture) as a colourless solid; MS: 482 (M+H)+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-6aec6ca7148c48079e4a241f710868a9
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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