Hydrochloric Acid → 2-Benzyloxycarbonylamino-3-(2,4-dichlorobenzenesulfonylamino)-2-methylpropionic Acid

HRID 1994434Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:30])([CH2:17][NH:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])(=[O:21])=[O:20])[C:13]([O:15]C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])(O)=O.[Na+].Cl>CO.O>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:30])([CH2:17][NH:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])(=[O:20])=[O:21])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

0.08 g (0.168 mmol) of methyl 2-benzyloxycarbonylamino-3-(2,4-dichlorobenzenesulfonylamino)-2-methylpropionate and 0.093 g (0.674 mmol) of potassium carbonate are stirred in a mixture of 4.5 ml of MeOH and 0.5 ml of water for 90 min. Then 3 ml of saturated NaHCO3 solution are added, and the mixture is stirred at 60° C. for 2 h. 0.5 ml of water is added, followed by 4N HCl (aq) until a pH of 2 is reached. The solution is extracted 3 times with 10 ml of EtOAc each time, the combined organic phases are dried over MgSO4, and the solvent is removed in vacuo. 68 mg of the desired product are obtained. MW=460 (calculated, monoisotopic), measured value: (M+H)+461.

Workup

extractionThe solution is extracted 3 times with 10 ml of EtOAc each time
dry with materialthe combined organic phases are dried over MgSO4
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-5b6693dda13d4be4b94dd3017b70533b
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652007B2

Reaction notes

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