Sodium Bicarbonate → HCID 68766963, compound

HRID 1170608Notes

Reaction equation

HRID 1170608 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CC(C)([O-])C.[K+].[C:25]([O:29][C:30](=[O:35])[CH2:31][CH2:32][CH2:33]Br)([CH3:28])([CH3:27])[CH3:26].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:25]([O:29][C:30](=[O:35])[CH2:31][CH2:32][CH2:33][O:17][C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 726987N-Carbobenzoxy-L-valineHCID 2757253tert-Butyl 4-bromobutanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 68766963HCID 68766963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-CBz-L-valine (16.25 g, 65 mmole) was dissolved in DMF (40 ml). To the solution was added potassium t-butoxide (7.24 g, 65 mmole). After 10 min, 4-bromobutyric acid t-butyl ester (12 g, 53 mmole) was added. The reaction mixture was kept at 65° C. for 2.5 hr and then poured into sodium bicarbonate aqueous solution and extracted with dichloromethane. The organic phase was dried and the product was isolated with silica gel column chromatography. 20.1 g.

Workup

  1. waitThe reaction mixture was kept at 65° C. for 2.5 hr
  2. extractionextracted with dichloromethane
  3. customThe organic phase was dried
  4. customthe product was isolated with silica gel column chromatography

Sources & evidence

ORD record
ord-6ef6c3e218124537af27c801777b815a
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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