Trifluoroacetic acid → methyl (2S)-2-amino-4-phenoxybutanoate

HRID 1807884Notes

Reaction equation

HRID 1807884 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@@H:4]([NH:14]C(OC(C)(C)C)=O)[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:22])[C@@H:4]([NH2:14])[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67178164(S)-2-tert-butoxycarbonylamino-4-phenoxy-butyric acid methyl ester

Product 1

HCID 67177678methyl (2S)-2-amino-4-phenoxybutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-tert-butoxycarbonylamino-4-phenoxy-butyric acid methyl ester (1.15 g) in dichloromethane (3 ml) was added under an argon atmosphere trifluoroacetic acid (4.2 ml). The mixture was stirred for 16 h. The mixture was concentrated. The residue was treated with sodium bicarbonate solution until the pH was basic and extracted with dichloromethane twice. The combined organic layers were dried (MgSO4) and evaporated. The product was used without purification for the next step, yellow oil. MS (ISP): 210.3 ([M+H]+)).

Workup

  1. concentrationThe mixture was concentrated
  2. additionThe residue was treated with sodium bicarbonate solution until the pH
  3. extractionextracted with dichloromethane twice
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customevaporated
  6. customThe product was used without purification for the next step, yellow oil

Sources & evidence

ORD record
ord-5ad5308f6ec64971b8a0dd126bc0b6e9
Source dataset
uspto-grants-2013_01
Patent number
US08357712B2

Reaction notes

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