Acetic Acid → N-Benzyloxycarbonyl-2-amino-2-[4-(1,4,7-trioxaoctyl)benzyl]-ethanol

HRID 1418788ノート

反応式

HRID 1418788 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][O:26][CH2:27][CH2:28][O:29][CH3:30])=[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][O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:19][CH:18]=1)[CH2:3][OH:2])=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 22940770N-benzyloxycarbonyl-3-[4-(1,4,7-trioxaoctyl)-phenyl]-alanine-methyl ester

生成物 1

HCID 67688276N-Benzyloxycarbonyl-2-amino-2-[4-(1,4,7-trioxaoctyl)benzyl]-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

7.35 g (17 mmol) of N-benzyloxycarbonyl-3-[4-(1,4,7-trioxaoctyl)-phenyl]-alanine-methyl ester (Example a) is dissolved in 35 ml of tert-butyl methyl ether and mixed with 0.9 g (23.8 mmol) of sodium borohydride. At 5° C., 10 ml of methanol is added, and it is stirred for four hours under argon at constant temperature. Then, 1.5 ml of acetic acid, dissolved in 5 ml of tetrahydrofuran, is added, mixed with 5 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.

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

出典と根拠

ORDレコード
ord-626cfba3432b454c9bf76f30c2a8a096
出典データセット
uspto-grants-1999_03
特許番号
US05885548

反応ノート

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