Triethylamine → (S)-2-((tert-Butoxycarbonyl)amino)-3-phenylpropyl methanesulfonate

HRID 507750ノート

反応式

HRID 507750 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:11][CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:29])=[O:28]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate

生成物 1

HCID 10065161(S)-2-((tert-Butoxycarbonyl)amino)-3-phenylpropyl methanesulfonate収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of (2S)-2-(tert-butoxycarbonylamino)-3-phenyl-1-propanol (3.0 g, 11.9 mmol) in anhydrous CH2Cl2 (120 mL) at 0° C. under a dry N2 atmosphere was treated with triethylamine (3.5 mL, 25.1 mmol) followed by dropwise addition of methanesulfonyl chloride (1.0 mL, 13.1 mmol). After stirring for 2 hours at 0° C., the solution was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated to a reduced volume (20 mL). The mixture was diluted with hexanes (100 mL) and allowed to stand at ambient temperature overnight. Colorless crystals were collected by filtration and dried under reduced pressure to provide the title compound (3.60 g, 92%). Rf=0.26 (hexanes:ethyl acetate, 2:1); 1H NMR (CDCl3) δ 7.36-7.18 (m, 5H), 4.71 (br s, 1H), 4.28-4.05 (m, 3H), 2.99-2.81 (m, 2H), 1.40 (s, 9H); MS (APCl+) m/z 254 (M+H)+.

後処理

  1. washthe solution was washed with brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to a reduced volume (20 mL)
  5. additionThe mixture was diluted with hexanes (100 mL)
  6. waitto stand at ambient temperature overnight
  7. filtrationColorless crystals were collected by filtration
  8. customdried under reduced pressure

出典と根拠

ORDレコード
ord-696f7653003e41c2befb8aea760c1ca3
出典データセット
uspto-grants-2010_08
特許番号
US07786153B2

反応ノート

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