4-Ethylphenyl isocyanate → 4-(2-Chlorobenzylamino)-3,3-dimethyl-4-oxobutyl 4-ethylphenylcarbamate

HRID 655956

Reaction equation

HRID 655956 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][NH:5][C:6](=[O:13])[C:7]([CH3:12])([CH3:11])[CH2:8][CH2:9][OH:10].[CH2:18]([C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1)[CH3:19]>C1COCC1.CN(C1C=CN=CC=1)C>[CH2:18]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:28])[O:10][CH2:9][CH2:8][C:7]([CH3:12])([CH3:11])[C:6]([NH:5][CH2:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=2[Cl:1])=[O:13])=[CH:22][CH:21]=1)[CH3:19]

Participants

5

Reactant 2

HCID 900074-Ethylphenyl isocyanateHCID 59778491N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamide

Product 1

HCID 250264164-(2-Chlorobenzylamino)-3,3-dimethyl-4-oxobutyl 4-ethylphenylcarbamateYield 25%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamide (400 mg, 1.6 mmol) in THF (25 mL) were added 4-ethylphenylisocyanate (276 μL, 1.92 mmol, 1.2 equiv.) and DMAP (293 mg, 2.4 mmol, 1.5 equiv.). The reaction mixture was stirred overnight. The reaction mixture was concentrated. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O, and further purified by flash column chromatography using a mixture of hexanes and EtOAc to give 4-(2-chlorobenzylamino)-3,3-dimethyl-4-oxobutyl 4-ethylphenylcarbamate (160 mg, 25%). LRMS (M+H+) m/z 403.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting residue was purified on RP-HPLC
  3. additiona mixture of acetonitrile and H2O
  4. customfurther purified by flash column chromatography
  5. additiona mixture of hexanes and EtOAc

Sources & evidence

ORD record
ord-5a3700b4a789410c9586979b71c72201
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Linked notes

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