Potassium Carbonate → HCID 21961241, compound

HRID 1445340Notes

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[OH:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:20][CH:21]1[CH:26]([O:27][C:28](=[O:30])[CH3:29])[CH:25]([O:31][C:32](=[O:34])[CH3:33])[CH:24]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[O:23][CH:22]1Br)(=[O:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl.O>[C:37]([O:36][CH2:35][CH:24]1[CH:25]([O:31][C:32](=[O:34])[CH3:33])[CH:26]([O:27][C:28](=[O:30])[CH3:29])[CH:21]([O:20][C:17](=[O:19])[CH3:18])[CH:22]([O:16][C:15]2[CH:14]=[CH:13][S:12][C:11]=2[C:9](=[O:10])[NH:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:23]1)(=[O:39])[CH3:38]

Participants

Conditions

Temperature: 22 °C

Procedure

1.12 g of N-benzyl-3-hydroxy-thiophene-2-carboxamide, 3.16 g of 4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl acetate, 3.30 g of potassium carbonate and 235 mg of benzyltributylammonium chloride were dissolved in 25 ml of dichloromethane, and 2.00 ml of water were added. The reaction mixture was stirred at 22° C. for 40 h. 50 ml of saturated sodium bicarbonate solution were added to the reaction mixture, which was extracted twice with 50 ml of dichloromethane each time. The combined organic phases were dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:1).

Workup

extractionwas extracted twice with 50 ml of dichloromethane each time
dry with materialThe combined organic phases were dried over magnesium sulfate
concentrationconcentrated
customThe crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:1)

Sources & evidence

ORD record: ord-c766fa5d03854dc39496352efec61947
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666848B2

Reaction notes

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