Sodium Sulfate → HCID 23378638, compound

HRID 1006559Notes

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-fe9227fb72d24b1a84a256fcc5c649cc
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790866B2

Reaction notes

Loading…