Dicyclohexylcarbodiimide → HCID 19917756, compound

HRID 1755639Notes

Reaction equation

HRID 1755639 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:43][C:44]1[S:45][CH:46]=[C:47]([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])[N:48]=1>>[CH2:53]([O:52][C:50]([CH2:49][C:47]1[N:48]=[C:44]([NH:43][C:17](=[O:19])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[S:45][CH:46]=1)=[O:51])[CH3:54]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 80170N-HydroxysuccinimideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

Product 1

HCID 19917756HCID 19917756, compoundYield 84.14%

Procedure

Alternatively, by working in a way similar to that above reported and by using N-tert-butoxycarbonyl-L-phenylalanine (10 g; 37.7 mmoles), N-hydroxysuccinimide (4.78 g; 41.5 mmoles), dicyclohexylcarbodiimide (8.56 g; 41.5 mmoles) and ethyl (2-amino-4-thiazolyl)acetate (7 g; 37.7 mmoles), a crude was obtained which, chromatographed on silica gel (eluent ligroin:ethyl acetate 6:4) and further crystallized from ligroin, afforded N-(4-ethoxycarbonylmethyl-2-thiazolyl)-3-phenyl-2-(tert-butoxycarbonyl)amino-propanamide (13.74 g; 84.14% yield).

Workup

  1. customa crude was obtained which
  2. customchromatographed on silica gel (eluent ligroin:ethyl acetate 6:4)
  3. customfurther crystallized from ligroin

Sources & evidence

ORD record
ord-7debc7b748be455590ac7c765279ff8d
Source dataset
uspto-grants-1995_08
Patent number
US05438046

Reaction notes

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