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

HRID 655944Notes

Reaction equation

HRID 655944 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[C:7]([CH3:11])([CH3:10])[CH2:8][OH:9].[CH2:17]([C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1)[CH3:18]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:17]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:27])[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]([NH:5][CH2:4][C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[Cl:1])=[O:12])=[CH:21][CH:20]=1)[CH3:18]

Participants

5

Reactant 2

HCID 900074-Ethylphenyl isocyanateHCID 59778447N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide

Product 1

HCID 597784683-(2-Chlorobenzylamino)-2,2-dimethyl-3-oxopropyl 4-ethylphenylcarbamateYield 21.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (30 mg, 0.12 mmol), in CH2Cl2 were added DMAP and 4-ethylphenylisocyanate (21 μL, 0.15 mmol, 1.5 equiv.). The reaction mixture was stirred for 1 h. The reaction mixture was concentrated. The resulting residue was to purify on RP-HPLC to give 3-(2-chlorobenzylamino)-2,2-dimethyl-3-oxopropyl 4-ethylphenylcarbamate (10 mg, 17%). LRMS (M+H+) m/z 389.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto purify on RP-HPLC

Sources & evidence

ORD record
ord-5902bfb0da7144359c909edba60c3015
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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