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

HRID 1459141
Notes
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Reaction equation

HRID 1459141 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 10993711pentafluorophenyl N-t-butyloxycarbonyl-L-phenylalaninateYield 99.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

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

  1. filtrationThe suspension was filtered
  2. customthe solvent was evaporated under reduced pressure from the filtrate
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationThe suspension was filtered
  5. customthe solvent was evaporated under reduced pressure from the filtrate

Sources & evidence

ORD record
ord-0959808ac14c4b9baa66a5aa79195e99
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05853713

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes