Boc-DL-phenylalanine methyl ester → Methyl 3-phenylpropionate

HRID 1721227Notes

Reaction equation

HRID 1721227 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4](NC(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.C(OC(OC(C)(C)C)N(C)C)(C)(C)C.CCOCC>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 1

HCID 3786800Boc-DL-phenylalanine methyl ester

Product 1

HCID 7643Methyl 3-phenylpropionate

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineSolvent

Procedure

A solution of 3.50 g of (S)-4-carboxymethyl)alpha-[[(1,1-dimethylethoxy)carbonyl]amino]benzenepropanoic acid methyl ester in 40 mL of dry toluene and 10 mL of dimethylformamide di-t-butyl acetal was heated to a bath temperature of 80° C. for 4 hours. After cooling, the mixture was diluted with 100 mL of ether and was washed with water and saturated sodium chloride solution and was dried over magnesium sulfate. The residue obtained after filtration and evaporation was chromatographed over 150 g of silica gel, eluting with 20% ethyl acetate-hexane to give 2.663 g of (S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-]2-(1,1-dimethylethoxy) 2-oxoethyl]benzenepropanoic acid methyl ester.

Workup

  1. temperatureAfter cooling
  2. washwas washed with water and saturated sodium chloride solution
  3. dry with materialwas dried over magnesium sulfate
  4. customThe residue obtained
  5. filtrationafter filtration and evaporation
  6. customwas chromatographed over 150 g of silica gel
  7. washeluting with 20% ethyl acetate-hexane

Sources & evidence

ORD record
ord-ff4b0757e39c40a291048bbad7351a96
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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