4-Ethylphenyl isocyanate → (S)-(1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate

HRID 655962Notes

Reaction equation

HRID 655962 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])=[O:7].[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1)[CH3:20]>C1COCC1>[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:29])[O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:6](=[O:7])[NH:5][CH2:4][C:3]2[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=2[Cl:1])=[CH:23][CH:22]=1)[CH3:20]

Participants

4

Reactant 2

HCID 900074-Ethylphenyl isocyanateHCID 59778476(S)-N-(2-chlorobenzyl)-2-(hydroxymethyl)pyrrolidine-1-carboxamide

Product 1

HCID 59778442(S)-(1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamateYield 10.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)—N-(2-chlorobenzyl)-2-(hydroxymethyl)pyrrolidine-1-carboxamide (268 mg, 1.0 mmol) in THF (2.0 mL) was added 4-ethyl-phenyl-isocyanate (220 mg, 1.5 mmol). The reaction mixture was stirred for 1 h. LC/MS indicated the reaction was complete. The reaction was concentrated and the resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give (S)-(1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate (42 mg, 10% for two steps). LRMS (M+H+) m/z 416.0.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe resulting residue was purified on RP-HPLC
  3. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-b4f6cb56f3f047e494dca0a367523914
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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