Ethyl Acetate → [(S)-1-benzyloxymethyl-2-(2-iodo-1,1-diphenylethoxy)-ethyl]-carbamic acid tert-butyl ester

HRID 20394

反応式

HRID 20394 の反応式
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:18][OH:19])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]1([C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[I:35]N1C(=O)CCC1=O.C(OCC)(=O)C>C(#N)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:18][O:19][C:27]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:28][I:35])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 107401,1-DiphenylethyleneHCID 120273N-IodosuccinimideHCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

生成物 1

HCID 68558007[(S)-1-benzyloxymethyl-2-(2-iodo-1,1-diphenylethoxy)-ethyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Dissolve ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (1.0 g, 3.55 mmol) and 1,1-diphenylethylene (0.534 g, 2.96 mmol) in acetonitrile (20 mL). Add N-iodosuccinimide (0.800 g, 3.55 mmol) and stir at room temperature 72 hours. Pour into ethyl acetate and wash with saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate. Purify on silica gel, eluting with 0:100 to 30:70 ethyl acetate:hexanes to give the desired compound.

後処理

  1. washwash with saturated aqueous sodium chloride
  2. dry with materialDry (magnesium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify on silica gel
  6. washeluting with 0:100 to 30:70 ethyl acetate

出典と根拠

ORDレコード
ord-d84c6867d5d949f78021d1ce8021af7c
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

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