Benzyl chloroformate → benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-hydroxyhexan-2-yl](3-methylbutyl)carbamate

HRID 1524347ノート

反応式

HRID 1524347 の反応式
[Si:1]([O:18][CH2:19][C@@H:20]([NH:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:21][CH2:22][CH2:23][CH2:24][OH:25])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl[C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39]>C(Cl)(Cl)Cl>[CH2:41]([O:40][C:38](=[O:39])[N:26]([C@@H:20]([CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 86708047(5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-5-[(3-methylbutyl)amino]hexan-1-ol

生成物 1

HCID 86708050benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-hydroxyhexan-2-yl](3-methylbutyl)carbamate収率 67.1%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a stirred solution of the material from Step 5 (8 g, 18.11 mmol) in a 2:1 mixture of chloroform and saturated aqueous NaHCO3 (271 mL) was added benzyl chloroformate (2.59 mL, 118.11 mmol). The reaction mixture was stirred at room temperature for 1 hour, partitioned and extracted with chloroform. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using EtOAc-hexanes (10 to 70%) to yield 7 g of the title compound. LCMS (M+1)=576

後処理

  1. custompartitioned
  2. extractionextracted with chloroform
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-2a5b393dc4c34cb6887016cd2e555922
出典データセット
uspto-grants-2015_07
特許番号
US09079834B2

反応ノート

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