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

HRID 1429405Notes

Reaction equation

HRID 1429405 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21877217Toluene methylene chlorideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-b8132475168d47799b0336f2c18ad427
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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