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Methanesulfonyl chloride → 2-(2-Benzyloxycarbonylamino-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1965157
ノート
印刷プレビュー

反応式

HRID 1965157 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH:10]([OH:21])[CH:9]1[CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][Si:14]([C:17]([CH3:18])([CH3:20])[CH3:19])([CH3:16])[CH3:15])[CH:10]([O:21][S:45]([CH3:44])(=[O:47])=[O:46])[CH:9]1[CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:7])([CH3:2])([CH3:3])[CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 675147812-(2-Benzyloxycarbonylamino-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 866659662-(2-Benzyloxycarbonylamino-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution containing crude 8 (500 mg, 1.01 mmol) in DCM (15 mL) was cooled to 0° C. DIPEA (261 mg, 2.02 mmol) was added followed by the addition of MsCl (117 mg, 1.02 mmol) and DMAP (13 mg, 0.1 mmol). After 2 h, the reaction mixture was warmed to ambient temperature, diluted with DCM, washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 578 mg (quant.) of crude 9 as a tan-colored foam which was used without further purification. 1H NMR (CDCl3, 300 MHz), mixture of rotomers: δ7.35 (m, 5H), 5.90 (m, 1H), 5.10 (m, 2H), 4.67 (m, 1H), 4.40 (m, 1H), 4.11 (m, 2H), 3.94 (m, 0.5H), 3.80 (m, 0.5H), 3.74 (app dd, J=12.2, 5.0 Hz, 1H), 3.51 (m, 0.5H), 3.31 (m, 0.5H), 3.02 (s, 3H), 1.96 (m, 0.5H), 1.85 (m, 0.5H), 1.46 (s, 9H), 0.88 (s, 9H), 0.05 (s, 6H) ppm. Mass spectrum, m/z [595.2] (M+Na)+.

後処理

  1. temperaturethe reaction mixture was warmed to ambient temperature
  2. washwashed successively with 1M HCl and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-d646846cfb754f6d85d131f98a1a00f0
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415486B2

反応ノート

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