N,O-Dimethylhydroxylamine → 1,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate

HRID 649728

반응식

HRID 649728 반응식
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20][NH:21][O:22][CH3:23].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:23][O:22][N:21]([CH3:20])[C:10](=[O:12])[C@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[NH:1][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

참가 물질

6

반응물 4

HCID 14232N,O-DimethylhydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

생성물 1

HCID 110559451,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of Boc-Phe-OH 5.1 (2.0 g, 7.53 mmol) and N,O dimethylhydroxylamine (808 mg, 8.29 mmol) in DCM (38 ml) was added TEA (2.2 ml, 15.8 mmol) and HOBT (1.27 g, 8.29 mmol). After cooling to 0° C., EDCI (1.59 g, 8.29 mmol) was added in one portion, and the reaction was stirred overnight, warming to room temperature. The reaction was concentrated in vacuo, diluted with EthOAc (150 ml), and washed with H2O, 1 N KHSO4, 1 N NaHCO3 and brine. After drying over Na2SO4, filtering, and concentrating in vacuo, the residue was purified by flash chromatography to give the title compound as an oil in 88% yield. Rf=0.35 (50% EthOAc/hexane). 1H NMR (300 MHz, CDCl3) δ7.28 (d, 2H, J=7.4 Hz), 7.24 (t, 1H, J=6.8 Hz), 7.17 (d, 2H, 7.1 Hz), 5.18 (d, 1H, J=7.4 Hz), 4.9 (dd, 1H, J=7.0, 11.9 Hz), 3.66 (s, 3H), 3.16 (s, 3H), 3.05 (dd, 1H, J=6.0, 13.6 Hz), 2.87 (dd, 1H, J=7.0, 13.6 Hz), 1.39 (s, 9H).

후처리

  1. temperaturewarming to room temperature
  2. concentrationThe reaction was concentrated in vacuo
  3. additiondiluted with EthOAc (150 ml)
  4. washwashed with H2O, 1 N KHSO4, 1 N NaHCO3 and brine
  5. dry with materialAfter drying over Na2SO4
  6. filtrationfiltering
  7. concentrationconcentrating in vacuo
  8. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-bd070c42e5024da69a098affb66e5c43
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06270957B1

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