Sodium Carbonate → L-Alanine 1,1-dimethylethyl ester

HRID 1666926Notes

Reaction equation

HRID 1666926 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl.[C:8]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH2:15])([CH3:11])([CH3:10])[CH3:9]>O.C(OCC)C>[C:8]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH2:15])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 89016L-Alanine 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of sodium carbonate (875 mg, 8.25 mmol, 5.0 equiv.) in deioned water (10 mL) and diethyl ether (10 mL) was added L-alanine tert-butyl ester hydrochloride (300 mg, 1.65 mmol, 1.0 equiv.). The resulting solution was stirred under an atmosphere of nitrogen for 1 hour. The aqueous phase was extracted with diethyl ether (3×10 mL) and the combined extracts were dried over MgSO4. The solvent was removed in vacuo to settle the title compounds as a colourless oil (200 mg, 84%); v(max) (film) 3377 (N—H), 2978 (C—H), 1729 (C═O) cm″1; δH (250 MHz, CDCl3) 3.42 (1H, q, J 7.02 Hz CH), 1.63 (2H, br, NH2), 1.46 (9H, s, (CH3)3), 1.29 (3H, d, J 7.02 Hz, CH3CH); δc (62.5 MHz, CDCl3) 177.1, 81.2, 51.0, 28.4, 21.2; [α]D20 +3.7 (c 0.97 CHCl3), (lit. [α]D24 +2.3 (c 1.00 CHCl3)).

Workup

  1. extractionThe aqueous phase was extracted with diethyl ether (3×10 mL)
  2. dry with materialthe combined extracts were dried over MgSO4
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ba004d6875a54cd3a5c7871c6bb25e1b
Source dataset
uspto-grants-2011_10
Patent number
US08044173B2

Reaction notes

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