tert-Butyl bromoacetate → HCID 69778026, compound

HRID 1634914Notes

Reaction equation

HRID 1634914 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:16])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:8])([CH3:4])[CH3:3].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>C(#N)C.P([O-])([O-])([O-])=O>[CH3:4][C:2]([O:5][C:6](=[O:16])[C@H:7]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH:8][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoate

Product 1

HCID 69778026HCID 69778026, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 6342AcetonitrileSolvent

Procedure

An emulsion of L-phenylalanine 1,1-dimethylethyl ester (compound prepared at point A) (53.53 g; 242 mol), tert-butyl bromoacetate (37.3 mL; 254 mol) in acetonitrile (400 mL) and 2M buffer phosphate pH 8 (200 mL) is vigorously stirred at room temperature for 16 hours. After separation, the organic phase is evaporated and the residue is taken up into EtOAc; the aqueous phase is extracted with EtOAc (3×200 mL). The combined organic phases are washed with water (2×300 mL), saline solution (200 mL) and finally dried over Na2SO4. The crude is purified by flash chromatography (n-hexane/EtOAc 9:1 to 75:25). After removing the solvents under vacuum, the desired compound is obtained as a colourless oil (66.04 g; 196.90 mol).

Workup

  1. customAfter separation
  2. customthe organic phase is evaporated
  3. extractionthe aqueous phase is extracted with EtOAc (3×200 mL)
  4. washThe combined organic phases are washed with water (2×300 mL), saline solution (200 mL)
  5. dry with materialfinally dried over Na2SO4
  6. customThe crude is purified by flash chromatography (n-hexane/EtOAc 9:1 to 75:25)
  7. customAfter removing the solvents under vacuum

Sources & evidence

ORD record
ord-6103305f2f624e7ab0f5b8fb28c340f1
Source dataset
uspto-grants-2003_01
Patent number
US06509324B1

Reaction notes

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