Water → HCID 86625212, compound

HRID 1010887Notes

Reaction equation

[OH:1][C@@H:2]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])=[CH:7][CH:6]=1)[CH2:3][OH:4].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.O>N1C=CC=CC=1>[CH3:31][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:4][CH2:3][C@H:2]([C:5]2[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:20])[CH3:12])=[CH:7][CH:6]=2)[OH:1])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4.32 g of the compound [5-2] was dissolved in 50 mL of pyridine, and 3.66 g of p-toluenesulfonyl chloride was added thereto under an ice-cold condition. The reaction mixture was stirred overnight at 0° C., water was added thereto, and then the mixture was extracted with ethyl acetate, and the resulting organic layer was dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=50/50-0/100), to obtain 6.52 g of (2S)-2-(4-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}phenyl)-2-hydroxyethyl 4-methylbenzenesulfonate [5-3] (hereinafter, referred to as the compound [5-3]) as a colorless amorphous.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialthe resulting organic layer was dried over anhydrous sodium sulfate
filtrationThe insolubles were filtered
concentrationthe filtrate was concentrated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=50/50-0/100)

Sources & evidence

ORD record: ord-04b2c68fae1047f19a538c6e3580bc44
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977336B2

Reaction notes

Loading…