Ammonia → ((S)-2-Benzyloxy-1-carbamoylethyl)carbamic acid tert-butyl ester

HRID 243014

반응식

HRID 243014 반응식
[CH2:1]([O:8][CH2:9][C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:23]1CCOCC1.C(OC(Cl)=O)C(C)C.N>C1COCC1>[C:18]([O:17][C:15](=[O:16])[NH:14][C@H:10]([C:11](=[O:12])[NH2:23])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:21])([CH3:20])[CH3:19]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

생성물 1

HCID 7216900((S)-2-Benzyloxy-1-carbamoylethyl)carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-15 °C

실험 절차

To a solution of (S)-3-benzyloxy-2-(tert butoxycarbonylamino)propionic acid (0.98 g, 3.3 mmol) in anhydrous THF (13 mL) at −15° C. was added N-methylmorpholine (0.4 mL, 3.3 mmol) and isobutylchloroformate (0.4 mL, 3.3 mmol) under a nitrogen atmosphere. After 2 minutes, 33% aqueous ammonia (0.3 mL, 5 mmol) was added and the resulting mixture stirred at −15° C. for 2 h. The reaction mixture was allowed to warm to RT and was partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The combined organic fractions were washed with aqueous 5% NaHCO3, water, dried (MgSO4) and concentrated in vacuo. The resulting white solid was used without further purification (quant. yield). 1H NMR (CDCl3, 300 MHz): δ 7.41-7.25 (5H, m), 6.42 (1H, br s), 5.48 (2H, br s), 4.55 (2H, dd, J=22., 12 Hz), 4.30 (1H, br s), 3.95-3.85 (1H, dd, J=9.5, 3.9 Hz), 3.55 (1H, dd, J=9.5, 6.7 Hz), 1.42 (9H, s).

후처리

  1. temperatureto warm to RT
  2. customwas partitioned between EtOAc
  3. washThe combined organic fractions were washed with aqueous 5% NaHCO3, water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting white solid was used without further purification (quant. yield)

출처 및 근거

ORD 기록
ord-63b88a027098472694eb86aa0231fc9c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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