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

HRID 488384

Reaction equation

HRID 488384 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:14]C(OC(C)(C)C)=O)[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22]O>>[CH3:22][O:13][C:11](=[O:12])[C@H:10]([NH2:14])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 2733693(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Product 1

HCID 13635389(2R)-3-benzyloxy-2-aminopropanoic acid methyl esterYield 100%

Procedure

A solution of (2R)-3-benzyloxy-2-(N-(t-butoxycarbonyl)amino)propanoic acid (23 g, 78 mmol, [α]D −4.4° (c=2, H2O )) in methanol (250 mL) was cooled to 0° C. and HCl (g) bubbled into the solution until saturated. The resulting mixture was stirred at ambient temperature for 17 hours and then concentrated in vacuo to afford 17 g (100% yield) of (2R)-3-benzyloxy-2-aminopropanoic acid methyl ester, a compound of formula (M), as a white solid; NMR (DMSO-d6) 8.7 (br s, 3), 7.4-7.3 (m, 5), 4.5 (q, 2), 4.4 (br s, 1), 3.8 (s, 2), 3.7 (s, 3) ppm.

Workup

  1. customHCl (g) bubbled into the solution until saturated
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4dc6de89b55b403a8650dd4bdc122851
Source dataset
uspto-grants-2005_12
Patent number
US06972290B2

Linked notes

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