Water → HCID 10161403, compound

HRID 1353150Notes

Reaction equation

[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][C:15]([CH3:34])=[C:16]([CH2:18][CH2:19][O:20][C:21]4[CH:30]=[CH:29][CH:28]=[C:27]5[C:22]=4[CH2:23][CH2:24][CH:25]=[C:26]5[CH2:31][CH2:32][OH:33])[N:17]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O>C(OCC)(=O)C.CS(C)=O.C(N(C(C)C)CC)(C)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[O:14][C:15]([CH3:34])=[C:16]([CH2:18][CH2:19][O:20][C:21]4[CH:30]=[CH:29][CH:28]=[C:27]5[C:22]=4[CH2:23][CH2:24][CH:25]=[C:26]5[CH2:31][CH:32]=[O:33])[N:17]=3)=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: -10 °C

Procedure

To a mixed solution of the compound (1.20 g) prepared in Example 3 in ethyl acetate (12 ml) and dimethylsulfoxide (5.0 ml), diisopropylethylamine (2.7 ml) was added, and a dimethylsulfoxide (6.5 ml) solution of sulfur trioxide-pyridine complex (1.25 g) was added dropwise thereto at −10° C., followed by stirring at −10° C. for 2 hours. The reaction mixture was poured into cold water, and extracted with ethyl acetate. The extract was washed with a saturated saline, dried with anhydrous magnesium sulfate, and concentrated to thereby obtain the crude title compound (1.57 g) having the following physical data. The obtained compound was used without purification in the subsequent reaction.

Workup

customat −10° C.
extractionextracted with ethyl acetate
washThe extract was washed with a saturated saline
dry with materialdried with anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-b5802c73f0a44b7bbabd70ef4763b1bc
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220864B2

Reaction notes

Loading…