Hydrochloric Acid → HCID 178441302, compound

HRID 1888682Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the product from Example 102 (50.0 mg, 0.127 mmol) and potassium hydroxide (71.5 mg, 1.27 mmol) in ethanol (1 mL) and water (0.2 mL) was heated to 60° C. for 24 hours. After cooling to ambient temperature, 1N HCl (aq) was added to adjust the pH to −1. The mixture was extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated by rotary evaporator to give a white solid. Recrystallization of the solid from ethyl acetate afforded 39.2 mg (75%) of the title compound. 1H NMR (DMSO-d6) δ 0.79 (s, 3H), 0.92 (t, J=7.2 Hz, 3H), 1.07 (br s, 3H), 1.18 (br s, 3H), 1.27-1.40 (m, 3H), 1.50-1.63 (m, 3H), 1.68 (s, 9H), 1.85 (br s, 1H), 2.51-2.59 (m, 2H), 2.91 (br s, 2H), 9.07 (br s, 1H), 12.10 (br s, 1H). MS (ESI+) m/z 411 (M+H)+.

Workup

temperatureAfter cooling to ambient temperature
extractionThe mixture was extracted with ethyl acetate
dry with materialThe extract was dried (MgSO4)
filtrationfiltered
concentrationconcentrated by rotary evaporator
customto give a white solid
customRecrystallization of the solid from ethyl acetate

Sources & evidence

ORD record: ord-a3fc3629195f4e40980221cd2d5de940
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501794B2

Reaction notes

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