Dicyclohexylcarbodiimide → HCID 54421670, compound

HRID 975962Notes

Reaction equation

HRID 975962 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:12][C@H:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][S:9]1.[CH3:20][Si:21]([CH3:42])([CH3:41])[CH2:22][CH2:23][O:24][C:25]([C:27]1[CH:28]=[C:29]([NH:33][C:34](=[O:40])[NH:35][CH2:36][C:37](O)=[O:38])[CH:30]=[CH:31][CH:32]=1)=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>>[C:16]([O:15][C:13]([C@@H:11]1[CH2:10][S:9][C@H:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:12]1[C:37](=[O:38])[CH2:36][NH:35][C:34](=[O:40])[NH:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[C:25]([O:24][CH2:23][CH2:22][Si:21]([CH3:42])([CH3:41])[CH3:20])=[O:26])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 19968011HCID 19968011, compoundHCID 22870470HCID 22870470, compound

Product 1

HCID 54421670HCID 54421670, compoundYield 33.6%

Procedure

2-Trimethylsilylethyl (2R,4R)-3-{3-{2-[4-tertbutoxycarbonyl]-2-(2-fluorophenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}benzoate may be prepared in a fashion similar to that described in Example 41 §A, but starting from 3.35 g of tert-butyl (2RS,4R)-2-(2-fluorophenyl)-4-thiazolidinecarboxylate, 4.0 g of 2-{3-[3-(2-trimethylsilylethoxycarbonyl)phenyl]ureido}acetic acid and 2.45 g of N,N'-dicyclohexylcarbodiimide. The crude product is purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (30/70 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. 2.4 g of 2-trimethylsilylethyl (2R,4R)-3-{3-{2-[4-tert-butoxycarbonyl-2-(2-fluorophenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}benzoate are thus obtained in the form of an amorphous beige solid, used as it is in subsequent syntheses ([α]D20 =±50.2°+1.6° (C=0.38%; CHCl3))

Workup

  1. custom2-Trimethylsilylethyl (2R,4R)-3-{3-{2-[4-tertbutoxycarbonyl]-2-(2-fluorophenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}benzoate may be prepared in a fashion similar to
  2. customThe crude product is purified by chromatography on silica [eluent: ethyl acetate/cyclohexane (30/70 by volume)]
  3. additionThe fractions containing the expected product
  4. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-9030636c8ffc4d8d8c0a920a2fbee775
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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