Dicyclohexylcarbodiimide → 2-{1(S)-[(9-fluorenylmethoxycarbonyl)amino]-2-methylpropyl}-5-methyl-4H-3,1-benzoxazin-4-one

HRID 1729243Notes

Reaction equation

HRID 1729243 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([NH:33][C@H:34]([C:38]([NH:40][C:41]3[CH:49]=[CH:48][CH:47]=[C:46]([CH3:50])[C:42]=3[C:43](O)=[O:44])=[O:39])[CH:35]([CH3:37])[CH3:36])=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([NH:33][C@H:34]([C:38]3[O:39][C:43](=[O:44])[C:42]4[C:46]([CH3:50])=[CH:47][CH:48]=[CH:49][C:41]=4[N:40]=3)[CH:35]([CH3:36])[CH3:37])=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 538591852-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methylbutanamido]-6-methylbenzoic acid

Product 1

HCID 186540022-{1(S)-[(9-fluorenylmethoxycarbonyl)amino]-2-methylpropyl}-5-methyl-4H-3,1-benzoxazin-4-oneYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

263 mg of N,N'-dicyclohexylcarbodiimide was added under ice-cooling to a solution of 401 mg of 2-{[N-(9-fluorenylmethoxycarbonyl)-L-valyl]amino}-6-methylbenzoic acid in 5 ml of N,N-dimethylformamide. After stirring for 3 hours, dicyclohexyl urea precipitated was filtered off and the filtrate was condensed. The residue was purified by a silica gel column chromatography (eluting solution: hexane-ethyl acetate) to afford 337 mg of 2-{1(S)-[(9-fluorenylmethoxycarbonyl)amino]-2-methylpropyl}-5-methyl-4H-3,1-benzoxazin-4-one, as a white foam. The physicochemical data are shown in Table 1.

Workup

  1. customdicyclohexyl urea precipitated
  2. filtrationwas filtered off
  3. customcondensed
  4. customThe residue was purified by a silica gel column chromatography (eluting solution: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d5953da93e014f1fbe395fdba48179df
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

Loading…