Water → HCID 178468877, compound

HRID 28390Notes

Reaction equation

HRID 28390 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].O>CN(C)C=O>[CH2:30]([O:29][C:27]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][CH:18]=2)[CH2:6][CH2:7]1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 178468873HCID 178468873, compound

Product 1

HCID 178468877HCID 178468877, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g (0.0008 mol) of trans-ethyl 4-(4-aminocyclohexyl)benzoate, 1.25 ml of triethylamine and 1.26 ml (0.0084 mol) of benzyl chloroformate at 95% in 40 ml of dimethylformamide is stirred at room temperature for 3 hours. The mixture is poured into water, extracted with ethyl acetate and dried, and the solvent is evaporated off. The residue is purified by chromatography on a silica gel column, eluting with an 8/2 cyclohexane/ethyl acetate mixture. The compound of the title is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried
  3. customthe solvent is evaporated off
  4. customThe residue is purified by chromatography on a silica gel column
  5. washeluting with an 8/2 cyclohexane/ethyl acetate mixture
  6. customThe compound of the title is obtained

Sources & evidence

ORD record
ord-f153600557c0416791bf202cd4833cdf
Source dataset
uspto-grants-2008_09
Patent number
US07419974B2

Reaction notes

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