4-Toluenesulfonyl chloride → tert-Butyl 1-(4-(2,2,2-trifluoro-1-(tosyloxyimino)ethyl)phenyl)ethylcarbamate

HRID 1961454Notes

Reaction equation

[F:1][C:2]([F:23])([F:22])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])=[CH:8][CH:7]=1)=[N:4][OH:5].CCN(C(C)C)C(C)C.[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:1][C:2]([F:22])([F:23])[C:3]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH3:13])=[CH:10][CH:11]=1)=[N:4][O:5][S:39]([C:36]1[CH:37]=[CH:38][C:33]([CH3:43])=[CH:34][CH:35]=1)(=[O:41])=[O:40]

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 1-(4-(2,2,2-trifluoro-1-(hydroxyimino)ethyl)phenyl)ethylcarbamate (640 mg, 1.93 mmol) was dissolved in CH2Cl2 (15 ml) together with DIPEA (367 μl, 2.11 mmol) and DMAP (23 mg, 0.19 mmol). The mixture was cooled to 0° C. before slow, portionwise addition of 4-toluenesulfonyl chloride (367 mg, 1.93 mmol). The reaction was allowed to reach room temperature over 2 h, washed with H2O (4*15 ml), dried over MgSO4, filtered and evaporated. The product was purified by flash chromatography using Pet. Ether/EtOAc (3:1) as eluent to give 817 mg (87%) of the title compound as pale solids.

Workup

washwashed with H2O (4*15 ml)
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe product was purified by flash chromatography

Sources & evidence

ORD record: ord-8a534d6cb8044b1a864d7972c98e4eff
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415333B2

Reaction notes

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