Water → (+/-)-1,1-Dimethylethyl [1-[[[(4-methylphenyl)-sulfonyl]oxy]methyl]-2-methylpropyl]carbamate

HRID 2217305Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC([N:16]([CH:20]([CH2:24][OH:25])[CH:21]([CH3:23])[CH3:22])[C:17](=[O:19])[OH:18])(C)C.O>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:25][CH2:24][CH:20]([NH:16][C:17](=[O:19])[O:18][C:2]([CH3:7])([CH3:3])[CH3:1])[CH:21]([CH3:22])[CH3:23])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 10 °C

Procedure

4-Methylbenzenesulfonyl chloride (0.2222 mol) was added portionwise at 10° C. to a mixture of 1,1-dimethylethyl [1-(hydroxymethyl)-2-methylpropyl]carbamic acid (ester) (0.202 mol) in pyridine (65 ml). The mixture was stirred at 10° C. for 2 hours. H2O (75 ml) was added at 10° C. The precipitate was filtered off, washed with H2O and taken up in CH2Cl2. The organic solution was washed with H2O, dried, filtered and the solvent was evaporated, yielding 49 g (68%) of (±)-1,1-dimethylethyl [1-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-2-methylpropyl]carbamate; mp. 85° C. (interm. 32).

Workup

filtrationThe precipitate was filtered off
washwashed with H2O
washThe organic solution was washed with H2O
customdried
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-22a44625827e47d785444296eb5b04af
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407969B2

Reaction notes

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