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Benzyl Bromide → N-[(1,1-dimethylethoxy)carbonyl]-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-L-phenylalanine phenylmethyl ester

HRID 393435
Notes
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Reaction equation

HRID 393435 reaction equation
[CH3:1][C:2]([CH3:37])([O:4][C:5]([NH:7][C@H:8]([C:34]([OH:36])=[O:35])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([O:19][CH2:20][CH:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])=[CH:12][CH:11]=1)=[O:6])[CH3:3].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C>[C:39]1([CH2:38][O:35][C:34](=[O:36])[C@H:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([O:19][CH2:20][CH:21]3[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:27]4[C:22]3=[CH:23][CH:24]=[CH:25][CH:26]=4)=[O:18])=[CH:14][CH:15]=2)[NH:7][C:5]([O:4][C:2]([CH3:37])([CH3:1])[CH3:3])=[O:6])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 2755959(S)-3-(4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)phenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Product 1

HCID 54069457N-[(1,1-dimethylethoxy)carbonyl]-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-L-phenylalanine phenylmethyl esterYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[(1,1-Dimethylethoxy)carbonyl]-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-L-phenylalanine (5.02 g, 10 mmol) and benzyl bromide (3.5 mL, 29 mmol) were stirred in DMF (25 mL) over KHCO3 (1.75 g, 17.5 mmol). After 18 hr, a white precipitate had formed. Most of the DMF was evaporated under reduced pressure, the residue was taken up in 100 mL of dichloromethane and was washed with water (2×50 mL). Most of the dichloromethane was evaporated and ether (100 mL) was added to precipitate the product. Filtration, washing with ether afforded N-[(1,1-dimethylethoxy)carbonyl]-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-L-phenylalanine phenylmethyl ester (5.3 g), mp 186-187° C.

Workup

  1. customa white precipitate had formed
  2. customMost of the DMF was evaporated under reduced pressure
  3. washwas washed with water (2×50 mL)
  4. customMost of the dichloromethane was evaporated
  5. additionether (100 mL) was added
  6. customto precipitate the product
  7. filtrationFiltration
  8. washwashing with ether

Sources & evidence

ORD record
ord-e9642957720144b7ad10463cae987339
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06806365B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes