Water → (+/-)-Acetic acid (1RS,3RS,4RS)-4-{[1-(4-butoxy-phenyl)-methanoyl]-amino}-3-(3,4-dimethoxy-phenyl)-cyclohexyl ester

HRID 2054432

Reaction equation

HRID 2054432 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9](=[O:11])[CH3:10])[CH2:4][CH:3]1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1.[CH2:22]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25].Cl.C(N=C=NCCCN(C)C)C.O>CN(C)C1C=CN=CC=1.ClCCl>[CH2:22]([O:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]([NH:1][CH:2]2[CH2:7][CH2:6][CH:5]([O:8][C:9](=[O:11])[CH3:10])[CH2:4][CH:3]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)=[O:32])=[CH:34][CH:35]=1)[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 962WaterHCID 729714-Butoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67022805acetic acid (1RS,3RS,4RS)-4-amino-3-(3,4-dimethoxyphenyl)cyclohexyl ester2×

Product 1

HCID 86601276(+/-)-Acetic acid (1RS,3RS,4RS)-4-{[1-(4-butoxy-phenyl)-methanoyl]-amino}-3-(3,4-dimethoxy-phenyl)-cyclohexyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

790 mg of (±)-acetic acid (1RS,3RS,4RS)-4-amino-3-3,4-dimethoxyphenyl)cyclohexyl ester (compound B1), 620 mg of 4-butoxybenzoic acid, 614 mg of N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride and 2 mg of 4-dimethylaminopyridine are stirred in 7 ml of dichloromethane for 18 h. 5 ml of water are added, the phases are separated and once the organic layer is extracted with 3 ml of dichloromethane. Then the organic layer is washed with 2.5 ml of saturated aqueous potassium bicarbonate solution and the aqueous solution is once extracted with 5 ml of dichloromethane. The combined organic layers are dried over magnesium sulfate, then the solvent is removed to give 1172 mg of the title compound as a colorless foam.

Workup

  1. customthe phases are separated
  2. extractiononce the organic layer is extracted with 3 ml of dichloromethane
  3. washThen the organic layer is washed with 2.5 ml of saturated aqueous potassium bicarbonate solution
  4. extractionthe aqueous solution is once extracted with 5 ml of dichloromethane
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. customthe solvent is removed

Sources & evidence

ORD record
ord-b264ffb0c9944122b5a11bd5f2bc3c0c
Source dataset
uspto-grants-2008_02
Patent number
US07329676B2

Linked notes

Loading…