3,4-Bis(cyclopropylmethoxy)benzoyl chloride → (+/-)-Acetic acid (1RS,3RS,4RS)-4-{[1-(3,4-bis-cyclopropylmethoxyphenyl)methanoyl]-amino}-3-(3,4-dimethoxyphenyl)cyclohexyl ester

HRID 2054431Notes

Reaction equation

HRID 2054431 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.[CH:22]1([CH2:25][O:26][C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=2[O:36][CH2:37][CH:38]2[CH2:40][CH2:39]2)[C:30](Cl)=[O:31])[CH2:24][CH2:23]1>C(Cl)Cl.C(N(CC)CC)C>[CH:22]1([CH2:25][O:26][C:27]2[CH:28]=[C:29]([C:30]([NH:1][CH:2]3[CH2:7][CH2:6][CH:5]([O:8][C:9](=[O:11])[CH3:10])[CH2:4][CH:3]3[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)=[O:31])[CH:33]=[CH:34][C:35]=2[O:36][CH2:37][CH:38]2[CH2:39][CH2:40]2)[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 179890793,4-Bis(cyclopropylmethoxy)benzoyl chlorideHCID 67022805acetic acid (1RS,3RS,4RS)-4-amino-3-(3,4-dimethoxyphenyl)cyclohexyl ester2×

Product 1

HCID 86601277(+/-)-Acetic acid (1RS,3RS,4RS)-4-{[1-(3,4-bis-cyclopropylmethoxyphenyl)methanoyl]-amino}-3-(3,4-dimethoxyphenyl)cyclohexyl esterYield 20.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

9.5 mmol of (±)-acetic acid (1SR,3RS,4RS)-4-amino-3-(3,4-dimethoxyphenyl)cyclohexyl ester (compound B2) are dissolved in a mixture of 40 ml of methylene chloride and 10 ml of triethylamine and treated with 8.9 mmol of 3,4-dicyclopropylmethoxybenzoyl chloride. After stirring for 1 h at room temperature, the reaction mixture is concentrated and the residue chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 4/4/1 as eluent. After concentration of the corresponding eluate fractions, 1.86 mmol of the title compound are obtained.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customthe residue chromatographed on silica gel using
  3. additiona mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 4/4/1 as eluent

Sources & evidence

ORD record
ord-bb5e5f9ea25a47e586b36e44e71c708b
Source dataset
uspto-grants-2008_02
Patent number
US07329676B2

Reaction notes

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