Acetic Acid → N-Benzyloxycarbonyl-2-amino-2-[4-propoxybenzyl]-ethanol

HRID 1459109

反応式

HRID 1459109 の反応式
C[O:2][C:3](=O)[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[BH4-].[Na+].CO.C(O)(=O)C>COC(C)(C)C.O1CCCC1.O>[CH2:9]([O:8][C:6]([NH:5][CH:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=1)[CH2:3][OH:2])=[O:7])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 22940772N-benzyloxycarbonyl-3-[4-propoxyphenyl]-alanine-methyl ester

生成物 1

HCID 67688130N-Benzyloxycarbonyl-2-amino-2-[4-propoxybenzyl]-ethanol

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

4.15 g (11.2 mmol) of N-benzyloxycarbonyl-3-[4-propoxyphenyl]-alanine-methyl ester is dissolved in 20 ml of tert-butyl methyl ether and mixed with 0.17 g (4.5 mmol) of sodium borohydride. At 0° C., 6 ml of methanol is added and it is stirred for three hours under argon at a temperature below 5° C. Then, 0.8 ml of acetic acid, dissolved in 3 ml of tetrahydrofuran, is added, mixed with 3 ml of water and stirred for ten minutes at room temperature. The organic phase is separated, washed with water and dried on sodium sulfate. The drying agent is suctioned off, the filtrate is concentrated by evaporation and the residue is chromatographed for purification on silica gel (eluent: ethyl acetate/hexane).

後処理

  1. additionis added
  2. stirringstirred for ten minutes at room temperature
  3. customThe organic phase is separated
  4. washwashed with water
  5. customdried on sodium sulfate
  6. concentrationthe filtrate is concentrated by evaporation
  7. customthe residue is chromatographed for purification on silica gel (eluent: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-ca274c22274d40b7a345efc0e30b3f31
出典データセット
uspto-grants-1998_12
特許番号
US05853699

関連ノート

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