Ammonia → 4-(2-(12-(Isopropylthio)dodecanoylamino)phenoxy)-butyramide

HRID 1604402Notes

Reaction equation

HRID 1604402 reaction equation
[CH:1]([S:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:18][C:19]1[CH:33]=[CH:32][CH:31]=[CH:30][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][C:25](OCC)=[O:26])=[O:17])([CH3:3])[CH3:2].[NH3:34].CO.C(Cl)Cl>CO>[CH:1]([S:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:18][C:19]1[CH:33]=[CH:32][CH:31]=[CH:30][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][C:25]([NH2:34])=[O:26])=[O:17])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 18796054Ethyl 4-(2-(12-(Isopropylthio)dodecanoylamino)-phenoxy)-butyrateHCID 21226129Dichloromethane methanol

Product 1

HCID 196031234-(2-(12-(Isopropylthio)dodecanoylamino)phenoxy)-butyramide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of (7) (20 mg, 0.041 mM) in methanol (10 mL) is added methanol saturated with ammonia (5 mL) and the stoppered mixture allowed to stir at ambient temperatures until TLC analysis shows little or no (D) remains. Concentration of the reaction mixture followed by preparative thin layer chromatography (silica gel; 3% methanol/methylene chloride as eluant) yields product 9 (11 mg) as a waxy solid.

Sources & evidence

ORD record
ord-0381e41e0b5649ebb28a5bff273bd744
Source dataset
uspto-grants-1999_11
Patent number
US05994362

Reaction notes

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