Sodium Hydroxide → (R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

HRID 857750Notes

Reaction equation

HRID 857750 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([O:16]C)=[O:15])[CH2:10][CH:11]1[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]1[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69656025HCID 69656025, compound

Product 1

HCID 2756015(R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acidYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl N-(tert-butoxycarbonyl)-3-cyclopropyl-D-alaninate (1.0 g, 4.1 mmol) in MeOH (25 mL) at 0° C. was added 1M NaOH (5.0 mL, 5.0 mmol) dropwise. After 1 h, the cold bath was removed, and the reaction followed by HPLC. After 5.5 h, the methanol was removed at reduced pressure, and the residue diluted with 15 mL water and washed with ether. The aqueous layer was acidified with cold 2M HCl and extracted with three portions of EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated at reduced pressure to give the title compound as a colorless oil (929 mg): 1H NMR (300 MHz, CDCl3): δ 5.10–5.22 (br d, J=6.1 Hz, 1H), 4.35–4.46 (m, 1H), 1.72 (t, J=6.2 Hz, 2H), 1.39 (s, 9H), 0.70–0.85 (m, 1H), 0.42–0.60 (m, 2H), 0.03–0.21 (m, 2H).

Workup

  1. customthe cold bath was removed
  2. waitAfter 5.5 h
  3. customthe methanol was removed at reduced pressure
  4. additionthe residue diluted with 15 mL water
  5. washwashed with ether
  6. extractionextracted with three portions of EtOAc
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-2d5d341732154fff93ffbd128943e7cd
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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