(2S)-4-amino-2-(((tert-butoxy)carbonyl)amino)butanoic acid → (S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-azaoctanedioic acid

HRID 976023ノート

反応式

HRID 976023 の反応式
[NH2:1][CH2:2][CH2:3][C@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5]([OH:7])=[O:6]>C(#N)C>[C:12]([O:11][C:9]([NH:8][C@@H:4]([CH2:3][NH:1][CH2:2][CH2:3][C@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5]([OH:7])=[O:6])[C:5]([OH:7])=[O:6])=[O:10])([CH3:15])([CH3:13])[CH3:14]

参加物

3

反応物 1

HCID 7019666(2S)-4-amino-2-(((tert-butoxy)carbonyl)amino)butanoic acid

生成物 1

HCID 57285280(S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-azaoctanedioic acid

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

A solution of (S)-4-amino-2-tert-butyloxycarbonylaminobutyric acid (1.03 g, 4.70 mmol) in acetonitrile (50 ml) was added to a solution of (S)-Boc-serine-β-lactone (0.80 g, 4.27 mmol) in acetonitrile (50 ml) and degassed H2O (50 ml). The pH was maintained at 5.5 by dropwise addition of 1M NaHCO3 with stirring. The mixture was stirred for 5 days at ambient temperature. The pH was controlled by NaHCO3 addition and the reaction monitored by TLC. The solvents were distilled off, the residue triturated with chloroform (5 ml), to which acetic acid was added to give pH 5. The chloroform solution was evaporated and the product isolated after chromatography on silica gel (CHCl3:MeOH 2:1).

後処理

  1. customdegassed H2O (50 ml)
  2. temperatureThe pH was maintained at 5.5 by dropwise addition of 1M NaHCO3
  3. stirringThe mixture was stirred for 5 days at ambient temperature
  4. additionThe pH was controlled by NaHCO3 addition
  5. distillationThe solvents were distilled off
  6. customthe residue triturated with chloroform (5 ml), to which acetic acid
  7. additionwas added
  8. customto give pH 5
  9. customThe chloroform solution was evaporated
  10. customthe product isolated after chromatography on silica gel (CHCl3:MeOH 2:1)

出典と根拠

ORDレコード
ord-ba29660763804d9eb3abe48ee51f82d8
出典データセット
uspto-grants-1997_03
特許番号
US05610141

反応ノート

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