Dicyclohexylcarbodiimide → pentafluorophenyl N-t-butyloxycarbonyl-L-phenylalaninate

HRID 53086Notes

Reaction equation

[CH3:1][C:2]([CH3:19])([O:4][C:5]([NH:7][C@H:8]([C:16]([OH:18])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH3:3].C1(N=C=NC2CCCCC2)CCCCC1.[F:35][C:36]1[C:41](O)=[C:40]([F:43])[C:39]([F:44])=[C:38]([F:45])[C:37]=1[F:46]>C(OCC)(=O)C>[F:35][C:36]1[C:41]([O:17][C:16](=[O:18])[C@H:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7][C:5]([O:4][C:2]([CH3:19])([CH3:1])[CH3:3])=[O:6])=[C:40]([F:43])[C:39]([F:44])=[C:38]([F:45])[C:37]=1[F:46]

Participants

Conditions

Temperature: 0 °C

Procedure

N-(1,1-Dimethylethoxycarbonyl)phenylalanine (6.36 g, 24 mmol) in ethyl acetate (50 mL) at 0° C. was added to dicyclohexylcarbodiimide (4.95 g, 24 mmol) and pentafluorophenol (4.42 g, 24 mmol) in ethyl acetate (50 mL) at 0° C. The mixture was stirred for 2.75 h at 0° C. The suspension was filtered and the solvent was evaporated under reduced pressure from the filtrate. The residue was dissolved in ethyl acetate. The suspension was filtered and the solvent was evaporated under reduced pressure from the filtrate to give N-(1,1-dimethylethoxycarbonyl)phenylalanine pentafluorophenyl ester (10.32 g, quantitative).

Workup

filtrationThe suspension was filtered
customthe solvent was evaporated under reduced pressure from the filtrate
dissolutionThe residue was dissolved in ethyl acetate
filtrationThe suspension was filtered
customthe solvent was evaporated under reduced pressure from the filtrate

Sources & evidence

ORD record: ord-5a31337fd9f246969d97e694b594fd14
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618528

Reaction notes

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