Hydrochloric Acid → HCID 56943062, compound

HRID 467995Notes

Reaction equation

C[O:2][C:3]([C:5]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2([C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[O:24])[CH2:22][CH2:21]2)[CH2:7][CH2:6]1)=[O:4].[OH-].[K+].Cl>CO.O>[CH3:29][S:26]([NH:25][C:23]([C:20]1([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]2([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]2)[CH2:21][CH2:22]1)=[O:24])(=[O:28])=[O:27]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution product of Example 36 (0.85 g, 1.97 mmol) in methanol (8.5 mL) was added KOH (0.39 g, 7.1 mmol) in water (2.1 mL) and the reaction mixture was stirred at 60° C. over a period of 16 h. The crude product obtained upon evaporation of the solvent was diluted with water (5.0 mL), acidified to pH=2 (1.5N HCl), extracted with ethyl acetate (100 mL×2). The organic layer was dried over sodium sulphate and concentrated. The residue obtained upon evaporation of the volatiles was purified by silica gel (230-400) column (25% ethyl acetate in petroleum ether) to give product as white solid 0.55 g (67%). mp: 97.5° C.-99.4° C.

Workup

customThe crude product obtained upon evaporation of the solvent
extractionextracted with ethyl acetate (100 mL×2)
dry with materialThe organic layer was dried over sodium sulphate
concentrationconcentrated
customThe residue obtained upon evaporation of the volatiles
customwas purified by silica gel (230-400) column (25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-5f901e8549b14fd786fd1be93afd0ac5
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623897B2

Reaction notes

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