Hydrochloric Acid → Acetic acid (1RS,3RS,4RS)-4-{[1-(4-methoxycarbonylphenyl)methanoyl]amino}-3-(3,4-dimethoxyphenyl)cyclohexyl ester

HRID 731684Notes

Reaction equation

HRID 731684 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.[CH3:22][O:23][C:24](=[O:34])[C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1.Cl.C(N=C=NCCCN(C)C)C.Cl>ClCCl>[CH3:22][O:23][C:24]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([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:30])=[CH:27][CH:26]=1)=[O:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 15513Monomethyl terephthalate2×HCID 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 86613661Acetic acid (1RS,3RS,4RS)-4-{[1-(4-methoxycarbonylphenyl)methanoyl]amino}-3-(3,4-dimethoxyphenyl)cyclohexyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.6 g of acetic acid (1RS,3RS,4RS)-4-amino-3-(3,4-dimethoxyphenyl)cyclohexyl ester (compound F1) are dissolved in 30 ml of dichloromethane. 982 mg (5.45 mmol) of terephthalic acid monomethyl ester and 1.25 g (6.74 mmol) of N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride are added successively under stirring. After 3 h further 18 mg (0.1 mmol) of terephthalic acid monomethyl ester are added. After 15 h the reaction is treated with aqueous hydrochloric acid and extracted several times with dichloromethane. After evaporation of the combined organic phases, the crude product is crystallized from ethyl acetate/cyclohexane to give 1.87 g (73% of theory) of the title compound as colourless solid.

Workup

  1. extractionextracted several times with dichloromethane
  2. customAfter evaporation of the combined organic phases
  3. customthe crude product is crystallized from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-56a5314b2d454dcf94107473db7f9e60
Source dataset
uspto-grants-2009_09
Patent number
US07585872B2

Reaction notes

Loading…