Potassium Carbonate → HCID 44626000, compound

HRID 1958682Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([C:21]([N:23]2[CH2:28][CH2:27][C:26]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:29]([NH2:31])=[O:30])[CH2:25][CH2:24]2)=[O:22])[S:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:45][CH2:46][CH2:47][OH:48]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([C:21]([N:23]2[CH2:24][CH2:25][C:26]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)([C:29]([NH2:31])=[O:30])[CH2:27][CH2:28]2)=[O:22])[S:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:45][CH2:46][CH2:47][OH:48])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 110 °C

Procedure

1 g of the compound obtained in stage 4B), 0.376 g of potassium carbonate and 0.223 g of 3-chloropropan-1-ol are added to 6 ml of DMF. The reaction medium is heated at 110° C. for 3 hours. The reaction medium is subsequently poured onto distilled water and the compound obtained is extracted with ethyl acetate. The organic phase is dried and evaporated. After purifying by chromatography on silica (eluent: CH2Cl2-MeOH (gradient from 0% to 4%)), 0.6 g of the expected compound is obtained.

Workup

additionThe reaction medium is subsequently poured
distillationonto distilled water
customthe compound obtained
extractionis extracted with ethyl acetate
customThe organic phase is dried
customevaporated
customAfter purifying by chromatography on silica (eluent: CH2Cl2-MeOH (gradient from 0% to 4%))

Sources & evidence

ORD record: ord-4539de32c66f411c9cd1f8a945121207
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410137B2

Reaction notes

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