Sodium Hydroxide → HCID 10257347, compound

HRID 1782775Notes

Reaction equation

[CH:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][C:22]=3[C:31]([NH:33][CH:34]3[CH2:39][CH2:38][CH2:37][CH:36]([C:40]([O:42]C)=[O:41])[CH2:35]3)=[O:32])=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[C:40]([CH:36]1[CH2:37][CH2:38][CH2:39][CH:34]([NH:33][C:31]([C:22]2[CH:23]=[C:24]([CH:29]=[CH:30][C:21]=2[O:20][CH2:19][CH2:18][CH2:17][C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:16][CH:15]=2)[C:25]([OH:27])=[O:26])=[O:32])[CH2:35]1)([OH:42])=[O:41]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 90.73 g of methyl 4-{3-[4-(3-cyclohexylpropoxy)phenyl]propoxy}-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate in 500 ml of THF and 500 ml of methanol is mixed with 300 ml of 2 molar sodium hydroxide solution and heated to 60° C. After one hour, the organic solvents are removed as far as possible in a rotary evaporator. 325 ml of 2 molar hydrochloric acid are added to the residue with stirring. A precipitate separates out during this and is filtered off with suction and washed with water. The product is purified by recrystallization from a mixture of 500 ml of acetone and 1000 ml of water. 77.5 g of product are obtained. m.p.: 160° C.

Workup

customthe organic solvents are removed as far as
custompossible in a rotary evaporator
addition325 ml of 2 molar hydrochloric acid are added to the residue
filtrationis filtered off with suction
washwashed with water
customThe product is purified by recrystallization from a mixture of 500 ml of acetone and 1000 ml of water

Sources & evidence

ORD record: ord-1ae4e980a4fb459295f4e4e2bc944e54
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498460B2

Reaction notes

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