Trifluoroacetic acid → (2R)-3-benzyloxy-2-aminopropanoic acid methyl ester

HRID 989519

Reaction equation

HRID 989519 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@@H:4]([CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:5]C(OC(C)(C)C)=O.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:22])[C@@H:4]([CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:5]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 54103156methyl (2R)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

Product 1

HCID 13635389(2R)-3-benzyloxy-2-aminopropanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyloxycarbonyl-O-benzyl-D-serine methyl ester (BF8-EZ0-275) (5.0 g, 16 mmol) stirring in dichloromethane (40 mL) and anisole (1 mL) at 0° C. was added trifluoroacetic acid (10 mL). After 4 h at room temperature, a saturated aqueous solution of sodium bicarbonate was added and the resulting mixture extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sufate, and concentrated. The crude product was used in the next step without further purification.

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sufate
  4. concentrationconcentrated
  5. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-11cb1c7d66fa4500a13e01441aaea8c8
Source dataset
uspto-grants-2003_10
Patent number
US06639076B1

Linked notes

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