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

HRID 1182103ノート

反応式

HRID 1182103 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7ea520ab8cd241e3bc08c9e2c61fb5ef
出典データセット
uspto-grants-2007_10
特許番号
US07288537B2

反応ノート

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