Sodium Cyanide → HCID 67640328、化合物

HRID 399515ノート

反応式

HRID 399515 の反応式
[C:1]([O:5][C:6](=[O:24])[C@@H:7]1[CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([CH3:4])([CH3:3])[CH3:2].[C-:25]#[N:26].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:24])[C@@H:7]1[CH2:11][C@H:10]([C:25]#[N:26])[CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 10861453HCID 10861453、化合物

生成物 1

HCID 67640328HCID 67640328、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of (4R)-1-(tert-butyloxycarbonyl)-4-(methane-sulfonyloxy)-L-proline tert-butyl ester (680 mg, 1.86 mmol) and sodium cyanide (912 mg, 18.6 mmol) in N,N-dimethylformamide (14 mL) was stirred for 16 hours at 80° C. under a nitrogen atmosphere. The cooled reaction mixture was diluted with ethyl acetate (100 mL), washed with water (2×), saturated brine solution, dried (Na2SO4), and evaporated. The crude product mixture was subjected to flash silica gel chromatography eluting with 20% ethyl acetate/hexane. Fractions containing the TLC less-mobile isomer were combined and evaporated to afford the desired title compound; yield 275 mg (50%). 400 MHz 1H NMR (CDCl3): δ1.42-1.48 (4s, 18H); 2.24 (m, 1H); 2.67 (m, 1H); 3.08 (m, 1H); 3.64 (m, 1H); 3.81-3.96 (m, 1H); 4.17-4.28 (m, 1H).

後処理

  1. customThe cooled reaction mixture
  2. washwashed with water (2×), saturated brine solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. washeluting with 20% ethyl acetate/hexane
  6. additionFractions containing the TLC less-mobile isomer
  7. customevaporated

出典と根拠

ORDレコード
ord-a3540fd27a934222ac2ca433182d46fe
出典データセット
uspto-grants-1998_10
特許番号
US05821261

反応ノート

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