Benzyl Alcohol → Benzyl 3-(t-butyloxycarbonylamino)benzoate

HRID 1646295Notes

Reaction equation

HRID 1646295 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=1)[C:12]([O:14][CH2:15][C:16]#N)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)[C:22]1[CH:27]=[CH:26]C=[CH:24][CH:23]=1>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=1)[C:12]([O:14][CH2:15][C:16]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 8520682Cyanomethyl 3-(t-butyloxycarbonylamino)benzoate

Product 1

HCID 10782446Benzyl 3-(t-butyloxycarbonylamino)benzoateYield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of cyanomethyl 3-(t-butyloxycarbonylamino)benzoate (20 g), triethylamine (10.6 g), 4-dimethylaminopyridine (0.1 g) and benzyl alcohol (11.4 g) is stirred at a bath temperature of 55° C. for 15 hours. The reaction mixture is extracted with ethyl acetate (200 ml), and the extract is washed with water, and ethyl acetate is distilled off under reduced pressure. The residue is recrystallized from 80% aqueous acetonitrile solution to give the title compound (22.0 g, 93%) as white short needles.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate (200 ml)
  2. washthe extract is washed with water, and ethyl acetate
  3. distillationis distilled off under reduced pressure
  4. customThe residue is recrystallized from 80% aqueous acetonitrile solution

Sources & evidence

ORD record
ord-d23eb321a0724ec8a37e83450ddfdc9f
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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