戴斯-马丁氧化剂 → 3(S)-(tert-butoxyformamido)-2-oxo-N-(1(S)-phenylpropyl)heptanamide

HRID 635639

反应方程式

HRID 635639 反应方程式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:46][CH2:47][CH2:48][CH3:49])[C@H:32]([OH:45])[C:33]([NH:35][C@H:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:37][CH3:38])=[O:34])=[O:29])([CH3:26])([CH3:25])[CH3:24]>ClCCl.C(OCC)(=O)C>[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:46][CH2:47][CH2:48][CH3:49])[C:32](=[O:45])[C:33]([NH:35][C@H:36]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:37][CH3:38])=[O:34])=[O:29])([CH3:26])([CH3:25])[CH3:24]

参与物

5

反应物 2

HCID 159087戴斯-马丁氧化剂2 次HCID 206399793(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamide

产物 1

HCID 206399773(S)-(tert-butoxyformamido)-2-oxo-N-(1(S)-phenylpropyl)heptanamide收率 70.6%

试剂、催化剂与溶剂 2

HCID 6344二氯甲烷溶剂HCID 8857乙酸乙酯溶剂

实验过程

0.383 g of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one was added to a solution of 0.285 g of 3(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamide in 20 ml of dichloromethane. The mixture was stirred at room temperature for 30 minutes and then a further 30 mg of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one were added. The mixture was stirred at room temperature for 30 minutes and then diluted with ethyl acetate. The solution was extracted with a solution of 10 g of sodium thiosulphate in 40 ml of saturated sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica gel using 20% ethyl acetate in hexane for the elution to give 200 mg of 3(S)-(tert-butoxyformamido)-2-oxo-N-(1(S)-phenylpropyl)heptanamide, MS: m/e 377.1 [M+H]+.

后处理

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. extractionThe solution was extracted with a solution of 10 g of sodium thiosulphate in 40 ml of saturated sodium bicarbonate solution
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel using 20% ethyl acetate in hexane for the elution

来源与证据

ORD记录
ord-1f96bf04c2014bce81f9c620da14c3a0
来源数据集
uspto-grants-2001_02
专利号
US06187905B1

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