Dicyclohexylcarbodiimide → HCID 86750875, compound

HRID 1781305Notes

Reaction equation

HRID 1781305 reaction equation
C(OC([NH:8][CH2:9][C:10]([N:12]1[C@H:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][S:14][CH:13]1[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:11])=O)(C)(C)C.C(C1N[C@H]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])CS1)C1C=CC=CC=1.C(OC(NCC(O)=O)=O)(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>>[C:46]([O:45][C:43]([CH:9]([NH2:8])[C:10]([N:12]1[C@H:16]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:15][S:14][CH:13]1[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:11])=[O:44])([CH3:49])([CH3:48])[CH3:47]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 53921609HCID 53921609, compoundHCID 86750876HCID 86750876, compound

Product 1

HCID 86750875HCID 86750875, compound

Procedure

B tert-Butyl (4R)-3-(2-tert-butoxycarbonylaminoacetyl)-2-benzyl-4-thiazolidinecarboxylate (isomer A) may be prepared in a manner similar to that described in Example 1C, but starting with 25.7 g of tert-butyl (2RS,4R)-2-benzyl-4-thiazolidinecarboxylate, 13.9 g of 2-tert-butoxycarbonylaminoacetic acid and 16.3 g of N,N'-dicyclohexylcarbodiimide. The crude product is purified by chromatography on silica [eluent: methylene chloride/methanol (99:1 by volume)]. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure at 40° C. 12.1 g of tert-butyl (4R)-3-(2-tert-butoxycarbonyl-aminoacetyl)-2-benzyl-4-thiazolidinecarboxylate (isomer A) are thereby obtained in the form of a cream-coloured foam, which is used in the subsequent syntheses without further treatment.

Workup

  1. customThe crude product is purified by chromatography on silica [eluent: methylene chloride/methanol (99:1 by volume)]
  2. additionThe fractions containing the expected product
  3. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-1643f581587c4ecfa782be2eff73af28
Source dataset
uspto-grants-1997_05
Patent number
US05633270

Reaction notes

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