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

HRID 1290705Notes

Reaction equation

HRID 1290705 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-19cc9b673f6346549d2772e9035e4e23
Source dataset
uspto-grants-1998_05
Patent number
US05753641

Reaction notes

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