Toluene → tert-butyl N-[(2R)-1-oxo-3-phenylpropan-2-yl]carbamate

HRID 1429405

反応式

HRID 1429405 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CO>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 637614Boc-D-phenylalanine methyl esterHCID 9855836Potassium sodium tartarate

生成物 1

HCID 7020444tert-butyl N-[(2R)-1-oxo-3-phenylpropan-2-yl]carbamate収率 89%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 21877217Toluene methylene chloride溶媒

実験手順

To a stirred solution of compound 31c (25.0 g, 90 mmol) in toluene-DCM (4:1, 1000 mL) was added dropwise a solution of DIBAL-H in toluene (1.0 M, 179 mL, 179 mmol) at −78° C. under argon and the mixture was stirred for 1 h at this temperature. Methanol (200 mL) was added immediately to quench the reaction. The reaction mixture was poured into a solution of 200 mL of 20% sodium potassium tartrate (Rochelle salt) and stirred at rt until the two layers separated. The organic layer was concentrated in vacuo and the residue was purified by CC (hexane/EA=2:1) to give compound 31d as a white solid (19.9 g, 89% yield).

後処理

  1. customto quench
  2. customthe reaction
  3. stirringstirred at rt until the two layers
  4. customseparated
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by CC (hexane/EA=2:1)

出典と根拠

ORDレコード
ord-b8132475168d47799b0336f2c18ad427
出典データセット
uspto-grants-2015_01
特許番号
US08940722B2

関連ノート

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