반응 #72420

반응 방정식

(S)-2-benzyloxycarbonylamino-3-methyl-butyric acid

N-methoxymethylamine hydrochloride

EDC.HCl

DIPEA

→

desired compound

수율 87.4%

[(S)-1-(Methoxy-methyl-carbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester

수율 87.4%

용매

DCM

DCM

반응 조건

후처리

1. 1
   세척washed with 1M HCl (aq) (3×200 mL), 1M NaOH (aq) (200 mL), sat. NaHCO3 (aq) (200 mL) and brine (300 mL)
2. 2
   건조The organic layer was dried over MgSO4
3. 3
   여과filtered
4. 4
   기타the solvent removed under vacuum

실험 절차

To (S)-2-benzyloxycarbonylamino-3-methyl-butyric acid (7) (50.0 g, 199 mmol), N-methoxymethylamine hydrochloride (38.8 g, 398 mmol) and EDC.HCl (47.7 g, 249 mmol) in DCM (500 mL) was added DIPEA (87 mL, 497 mmol) and the reaction mixture stirred at ambient temperature for 20 h, after which time the reaction mixture was diluted with DCM (200 mL), washed with 1M HCl (aq) (3×200 mL), 1M NaOH (aq) (200 mL), sat. NaHCO3 (aq) (200 mL) and brine (300 mL). The organic layer was dried over MgSO4, filtered and the solvent removed under vacuum to give the desired compound as a colourless oil (51.2 g, 87%); (AnalpH2_MeOH—4 min) Rt 2.76 min; m/z 295 (MH)+.

출처