Water → 2-[1(S)-[[N-(9-fluorenylcarbonyl)glycyl]amino]-2-methylpropyl]-5-methyl-4H-3,1-benzoxazin-4-one

HRID 1729250Notes

Reaction equation

O.[CH:2]1[C:14]2[CH:13]([C:15]([NH:17][CH2:18][C:19]([NH:21][C@H:22]([C:26]([NH:28][C:29]3[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:30]=3[C:31]([OH:33])=O)=[O:27])[CH:23]([CH3:25])[CH3:24])=[O:20])=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1>CN(C)C=O>[CH:11]1[C:12]2[CH:13]([C:15]([NH:17][CH2:18][C:19]([NH:21][C@H:22]([C:26]3[O:27][C:31](=[O:33])[C:30]4[C:34]([CH3:38])=[CH:35][CH:36]=[CH:37][C:29]=4[N:28]=3)[CH:23]([CH3:24])[CH3:25])=[O:20])=[O:16])[C:14]3[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

33 mg of water-soluble carbodiimide hydrochloride was added under ice-cooling to a solution of 72 mg of 2-[[[N-(9-fluorenylcarbonyl)glycyl]-L-valyl]amino]-6-methylbenzoic acid in 3 ml of N,N-dimethylformamide. The mixture was stirred at 0° C. for 0.5 hour and, then, at room temperature for 18 hours. The mixture was concentrated to give a residue which was purified by a silica gel column chromatography (eluting solution: methylene chlorideether) to afford 60 mg of 2-[1(S)-[[N-(9-fluorenylcarbonyl)glycyl]amino]-2-methylpropyl]-5-methyl-4H-3,1-benzoxazin-4-one as a white powder (see Table 1).

Workup

waitat room temperature for 18 hours
concentrationThe mixture was concentrated
customto give a residue which
customwas purified by a silica gel column chromatography (eluting solution: methylene chlorideether)

Sources & evidence

ORD record: ord-e6d24b865fde4f0db9d61fbcb237824f
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05332734

Reaction notes

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