Sodium Sulfate → HCID 23378638, compound

HRID 1279622Notes

Reaction equation

[C:1]1([S:7]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][C:12]=2[O:21][CH3:22])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CCCCCC.CCOCC>[C:1]1([S:7]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([CH2:15][OH:16])=[CH:13][C:12]=2[O:21][CH3:22])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of methyl 4-phenylsulfonylamino-3-methoxybenzoate (1.5 g; prepared in Reference Example 37.) in THF (90 ml) was cooled to −78° C. in a stream of argon. The solution of diisobutylaluminum hydride (1.0 M) in hexane (22 ml) was added dropwise thereto. The mixture was stirred for 4 hours at −78° C. After the temperature increased to room temperature, the mixture was diluted with ether (100 ml). A saturated aqueous sodium sulfate (1.5 ml) was added thereto slowly. The mixture was stirred for 30 minutes, dried over, filtered and concentrated to give the title compound (1.5 g)

Workup

temperatureAfter the temperature increased to room temperature
stirringThe mixture was stirred for 30 minutes
customdried over,
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-6a759b7506e340879dcf0433252664a9
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448290B1

Reaction notes

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