Triethylamine → {(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-carbamic acid tert-butyl ester

HRID 1182103노트

반응식

HRID 1182103 반응식
Cl.[Cl:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH:8]2[CH2:11][NH:10][CH2:9]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:21]([O:25][C:26](=[O:35])[NH:27][C@H:28]([CH2:32][O:33][CH3:34])[CH2:29][CH2:30]I)([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O>[C:21]([O:25][C:26](=[O:35])[NH:27][C@H:28]([CH2:32][O:33][CH3:34])[CH2:29][CH2:30][N:10]1[CH2:9][CH:8]([O:7][C:6]2[CH:12]=[CH:13][C:3]([Cl:2])=[CH:4][CH:5]=2)[CH2:11]1)([CH3:22])([CH3:24])[CH3:23]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 573501973-(4-Chlorophenoxy)azetidine hydrochlorideHCID 86600851((s)-3-Iodo-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester

생성물 1

HCID 69411661{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-(4-Chloro-phenoxy)-azetidine hydrochloride (0.669 g, 3.04 mmol), triethylamine (1.7 ml, 12.16 mmol) and [(S)-3-Iodo-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester (1.0 g, 3.04 mmol) in dimethylformamide (10 ml) is stirred at ambient temperature for 18 hours, then partitioned between ethylacetate and water. The ethylacetate phase is washed with saturated aqueous sodium bicarbonate solution and brine, dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution with a 5:95 methanol/dichloromethane) to afford {(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-carbamic acid tert-butyl ester as a clear oil. [MH]+ 385.25.

후처리

  1. custompartitioned between ethylacetate and water
  2. washThe ethylacetate phase is washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography (
  6. washelution with a 5:95 methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-7ea520ab8cd241e3bc08c9e2c61fb5ef
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288537B2

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