Dicyclohexylcarbodiimide → HCID 54132057, compound

HRID 1781316Notes

Reaction equation

HRID 1781316 reaction equation
C(OC([CH:8]([NH2:35])[C:9]([N:11]1[C@H:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][S:13][C@@H:12]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:10])=O)(C)(C)C.C1(C2C=CC=CC=2C2N[C@H]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])CS2)C=CC=CC=1.C(OC(NCC(O)=O)=O)(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>>[C:56]([O:55][C:53]([NH:35][CH2:8][C:9]([N:11]1[C@H:15]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:14][S:13][C@@H:12]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:10])=[O:54])([CH3:59])([CH3:58])[CH3:57]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 54115552HCID 54115552, compoundHCID 86750880HCID 86750880, compound

Product 1

HCID 54132057HCID 54132057, compound

Procedure

C tert-Butyl (2R,4R)-3-(2-tert-butoxycarbonyl-aminoacetyl)-2-(2-phenylphenyl)-4-thiazolidinecarboxylate may be prepared in a manner similar to that described in Example 1C, but starting with 5.44 g of tert-butyl (2RS,4R)-2-(2-phenylphenyl)-4-thiazolidinecarboxylate, 2.8 g of 2-tert-butoxycarbonylaminoacetic acid and 3.3 g of N,N'-dicyclohexylcarbodiimide. The crude product is purified by chromatography on silica [eluent: cyclohexane/ethyl acetate (80:20 by volume)]. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure at 40° C. 4.42 g of tert-butyl (2R,4R)-3-(2-tert-butoxycarbonylaminoacetyl)-2-(2-phenylphenyl)-4-thiazolidinecarboxylate are thereby obtained in the form of a white foam, which is used in the subsequent syntheses without further treatment.

Workup

  1. customThe crude product is purified by chromatography on silica [eluent: cyclohexane/ethyl acetate (80:20 by volume)]
  2. additionThe fractions containing the expected product
  3. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-acb9658cde0548e0a200ac19f404869d
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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