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Dicyclohexylcarbodiimide → Benzyl 5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate

HRID 989996
Notes
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Reaction equation

HRID 989996 reaction equation
[OH:1][CH:2]([CH2:15][OH:16])[CH:3]=[CH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[C:17]([NH:34][C@H:35]([C:39](O)=[O:40])[CH:36]([CH3:38])[CH3:37])([O:19][CH2:20][CH:21]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[C:17]([NH:34][C@H:35]([C:39]([O:16][CH2:15][CH:2]([OH:1])[CH:3]=[CH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])=[O:40])[CH:36]([CH3:37])[CH3:38])([O:19][CH2:20][CH:21]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 688217FMOC-L-valineHCID 54529065Benzyl 4,5-dihydroxy-2-pentenoate

Product 1

HCID 54039988Benzyl 5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent
2×

Conditions

Temperature
10 °C

Procedure

A mixture of benzyl 4,5-dihydroxy-2-pentenoate (4.4 g, 20 mmole), N-FMOC-L-valine (5.8 g, 17 mmole) and DMAP (0.21 g, 1.7 mmole) in 100 ml dichloromethane was cooled to about 10° C. A solution of DCC (4.2 g, 20 mmole) in 25 ml dichloromethane was added dropwise at the same temperature and the mixture was stirred overnight at room temperature. The mixture was cooled to 5° C. and the urethane was filtered. The filtrate was evaporated under reduced pressure and the product was isolated by silica gel column chromatography. Yield: 6.6 g=71%

Workup

  1. temperatureThe mixture was cooled to 5° C.
  2. filtrationthe urethane was filtered
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-89a89f6a177147aba1c45018eb0c03db
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06458772B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes