Dimethylformamide → HCID 69597605, compound
Reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].CN(C)C=O.C(N(CC)CC)C.[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>Cl>[C:2]([O:6][C:7](=[O:10])[CH2:8][NH:9][S:37]([C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:36][CH:35]=1)(=[O:39])=[O:38])([CH3:5])([CH3:4])[CH3:3]Participants
Procedure
To a mixture of glycine tert butyl ester hydrochloride salt (compound of formula XIV, 50 g, 300 mmol) and dimethylformamide (400 ml) at about 0° C. was added triethylamine (127 ml, 885 mmol) and 4-benzyloxybenzenesulfonyl chloride (102 g, 357 mmol). After stirring for about 1 hour, the mixture was warmed to a temperature of about 20° C. to about 25° C., and stirred for about an additional 12 hours. The mixture was diluted with 1M hydrochloric acid, extracted twice with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Trituration of the residue with ether-hexane afforded 91 g of [4-Benzyloxybenzenesulfonylamino]-acetic acid tert-butyl ester (compound of formula XV) as a colorless solid.
Workup
- temperaturethe mixture was warmed to a temperature of about 20° C. to about 25° C.
- stirringstirred for about an additional 12 hours
- extractionextracted twice with ethyl acetate
- dry with materialthe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7cae2be18c474d9abc3bf7f63b37d5c1
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07030242B2
Reaction notes
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