Water → Methyl 4-{[1-(2-{2-[(4-cyclohexylbenzyl)oxy]phenyl}ethyl)-6-methoxy-6-oxo-hexyl]amino}benzoate

HRID 2243303Notes

Reaction equation

HRID 2243303 reaction equation
[CH:1]1([C:7]2[CH:32]=[CH:31][C:10]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:19][CH2:20][C:21](=O)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:33][C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1.[Na].O>ClCCCl.Cl[Ti](Cl)(Cl)Cl>[CH:1]1([C:7]2[CH:32]=[CH:31][C:10]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:19][CH2:20][CH:21]([NH:33][C:34]3[CH:35]=[CH:36][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:42][CH:43]=3)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 12082Methyl 4-aminobenzoateHCID 5360545SodiumHCID 59210668Methyl 8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-oxooctanoate

Product 1

HCID 59210761Methyl 4-{[1-(2-{2-[(4-cyclohexylbenzyl)oxy]phenyl}ethyl)-6-methoxy-6-oxo-hexyl]amino}benzoate

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

At 0° C., 217 mg (1.15 mmol) of TiCl4 (1 M in CH2Cl2) were added to a solution of 500 mg (1.15 mmol) of methyl 8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-oxo-octanoate XIV and 190 mg (1.26 mmol) of methyl 4-aminobenzoate in 12.5 ml of 1,2-dichloroethane. The mixture was stirred at room temperature for 20 min, and 383 mg (1.72 mmol) of sodium triacetoxyborhydride were then added. The progress of the reaction was monitored by thin-layer chromatography, and after the reaction had ended, water was added. The mixture was extracted with ethyl acetate and the combined organic phases were dried over Na2SO4. The product was purified chromatographically (silica gel, gradient cyclohexane/ethyl acetate 10:1 to 0:100).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. customThe product was purified chromatographically (silica gel, gradient cyclohexane/ethyl acetate 10:1 to 0:100)

Sources & evidence

ORD record
ord-e571f6db65944787b9e060a705f26673
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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