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

HRID 1429405

반응식

HRID 1429405 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 21877217Toluene methylene chloride용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b8132475168d47799b0336f2c18ad427
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940722B2

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