Triethylamine → (R)-tert-Butyl 1-azido-3-methoxypropan-2-ylcarbamate

HRID 711540노트

반응식

HRID 711540 반응식
CS(Cl)(=O)=O.O[CH2:7][C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][O:10][CH3:11].CCN(CC)CC.[N-:27]=[N+:28]=[N-:29].[Na+]>C(Cl)Cl.CCOC(C)=O>[N:27]([CH2:7][C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][O:10][CH3:11])=[N+:28]=[N-:29]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 15287812N-Boc-(R)-2-amino-3-methoxy-1-propanol

생성물 1

HCID 86654731(R)-tert-Butyl 1-azido-3-methoxypropan-2-ylcarbamate수율 64.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

Methanesulfonyl chloride (4.0 g, 35 mmol) in DCM (50 mL) was slowly added to a solution of (R)-tert-butyl 1-hydroxy-3-methoxypropan-2-ylcarbamate (6.0 g, 29 mmol) and Et3N (3.64 g, 36 mmol) in DCM (150 mL) at 0° C. The reaction mixture was stirred at RT for 2 h. The organic phase was washed with water and saturated aq NaHCO3, concentrated, and dissolved in DMF. Sodium azide (2.34 g, 36.0 mmol) was added, and the reaction mixture was stirred at 75° C. for 4 h. The reaction mixture was diluted by EtOAc and washed with water. The crude product was purified by column chromatography on silica gel eluting with EtOAc and petroleum ether (EtOAc/PE=2/1) to give the title compound (4.3 g, 64%). 1H NMR (400 MHz, CDCl3) δ ppm 4.92 (s, 1H), 3.91 (m, 1H), 3.53-3.48 (m, 2H), 3.45-3.40 (m, 2H), 3.38 (s, 3H), 1.47 (s, 9H).

후처리

  1. washThe organic phase was washed with water and saturated aq NaHCO3
  2. concentrationconcentrated
  3. dissolutiondissolved in DMF
  4. stirringthe reaction mixture was stirred at 75° C. for 4 h
  5. washwashed with water
  6. customThe crude product was purified by column chromatography on silica gel eluting with EtOAc and petroleum ether (EtOAc/PE=2/1)

출처 및 근거

ORD 기록
ord-8e04af24ea004419a37634aafeac2950
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181255B2

반응 노트

불러오는 중…