Dicyclohexylcarbodiimide → HCID 18654003, compound

HRID 1729244Notes

Reaction equation

HRID 1729244 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:39]([NH:41][C:42]3[CH:50]=[CH:49][CH:48]=[C:47]([CH3:51])[C:43]=3[C:44]([OH:46])=[O:45])=O)[CH2:35][CH:36]([CH3:38])[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>C(OCC)(=O)C>[CH:25]1[C:26]2[CH:27]([CH2:29][O:30][C:31]([NH:33][C@H:34]([C:39]3[O:46][C:44](=[O:45])[C:43]4[C:47]([CH3:51])=[CH:48][CH:49]=[CH:50][C:42]=4[N:41]=3)[CH2:35][CH:36]([CH3:38])[CH3:37])=[O:32])[C:28]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 53779305HCID 53779305, compound

Product 1

HCID 18654003HCID 18654003, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

69 mg of N,N'-dicyclohexylcarbodiimide was added under ice-cooling to a solution of 163 mg of 2-{[N-(9-fluorenylmethoxycarbonyl)-L-leucyl]amino}-6-methylbenzoic acid in 4 ml of ethyl acetate. After stirring overnight, dicyclohexylurea precipitated was filtered off and the filtrate was concentrated. The residue was purified by a silica gel column chromatography (eluting solution: hexane-ethyl acetate) to give 110 mg of 2-{1(S)-[(9-fluorenylmethoxycarbonyl)amino]-3-methylbutyl}-5-methyl-4H-3,1-benzoxazine-4-one. The physicochemical data are shown in Table 1.

Workup

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

Sources & evidence

ORD record
ord-282c9b80c9e940eeb177d2571c3bb2d5
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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