Water → HCID 178486043、化合物

HRID 25581ノート

反応式

HRID 25581 の反応式
[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][OH:18])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22].N1C=CC=CC=1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]#[C:16][CH2:17][O:18][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:13][CH2:14]1)=[O:19])([CH3:3])([CH3:2])[CH3:4]

参加物

7

反応物 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178486040HCID 178486040、化合物

生成物 1

HCID 178486043HCID 178486043、化合物収率 65%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 520 mg (1.95 mmol) of trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 14 ml CH2Cl2 was treated at 0° C. with 0.17 ml (2.14 mmol) methanesulfonylchloride, 0.235 ml (2.92 mmol) pyridine and 238 mg (1.95 mmol) DMAP. The reaction mixture was warmed up over night to room temperature, water (2 ml) was added and the reaction was stirred for 5 min. After extraction with aqueous 10% KHSO4/Et2O (3×) the organic phases were washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl, dried over Na2SO4 and evaporated to yield 435 mg (65%) of trans-Methanesulfonic acid 3-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyl]-prop-2-ynyl ester, MS: 345 (M).

後処理

  1. extractionAfter extraction with aqueous 10% KHSO4/Et2O (3×) the organic phases
  2. washwere washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated

出典と根拠

ORDレコード
ord-793fb0110fba4dada34d375e4c77e623
出典データセット
uspto-grants-2005_02
特許番号
US06858651B2

反応ノート

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