Hydrochloric Acid → HCID 86695211, compound
Reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:21][CH2:20][C:19]2[S:18][C:17]3[C:12](=[C:13]([O:22][CH:23]4[CH2:28][CH2:27][CH:26]([N:29]5[CH2:35][C:31]6([CH2:34][O:33][CH2:32]6)[CH2:30]5)[CH2:25][CH2:24]4)[N:14]=[CH:15][N:16]=3)[C:11]1=2)(C(C)(C)C)(C)C.Cl>CO>[CH2:32]1[C:31]2([CH2:35][N:29]([CH:26]3[CH2:27][CH2:28][CH:23]([O:22][C:13]4[N:14]=[CH:15][N:16]=[C:17]5[C:12]=4[C:11]4[C@@H:10]([CH2:9][OH:8])[CH2:21][CH2:20][C:19]=4[S:18]5)[CH2:24][CH2:25]3)[CH2:30]2)[CH2:34][O:33]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (3S)-3-[[(tert-butyldimethylsilyl)oxy]methyl]-12-[(4-[2-oxa-6-azaspiro[3.3]heptan-6-yl]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraene (360 mg, 0.70 mmol, 1.00 equiv) in methanol (65 mL) was added 0.04 M aqueous hydrochloric acid (13 mL) at 0° C. The resulting solution was stirred for 4 h at 0° C. and then quenched with saturated aqueous sodium bicarbonate. The resulting solution was extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The solvents were evaporated under reduced pressure to yield 250 mg (crude) of the desired [(3S)-12-[(4-[2-oxa-6-azaspiro[3.3]heptan-6-yl]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]methanol as a colorless oil.
Workup
- customquenched with saturated aqueous sodium bicarbonate
- extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customThe solvents were evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-68e61decda80481894bba401ea28db96
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212190B2
Reaction notes
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