Hydrochloric Acid → HCID 86695189, compound

HRID 1504030Notes

Reaction equation

HRID 1504030 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:21][CH2:20][C:19]2[S:18][C:17]3[N:16]=[CH:15][N:14]=[C:13]([O:22][CH:23]4[CH2:32][CH2:31][C:26]5(OCC[O:27]5)[CH2:25][CH2:24]4)[C:12]=3[C:11]1=2)(C(C)(C)C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[OH:8][CH2:9][C@H:10]1[CH2:21][CH2:20][C:19]2[S:18][C:17]3[N:16]=[CH:15][N:14]=[C:13]([O:22][CH:23]4[CH2:32][CH2:31][C:26](=[O:27])[CH2:25][CH2:24]4)[C:12]=3[C:11]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131734320HCID 131734320, compound

Product 1

HCID 86695189HCID 86695189, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S)-3-[[(tert-butyldimethylsilyl)oxy]methyl]-12-[1,4-dioxaspiro[4.5]decan-8-yloxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraene (840 mg, 1.76 mmol, 1.00 equiv) in THF (20 mL) was added hydrochloric acid (3 M, 10 mL) at 0° C. and stirred overnight at room temperature. The pH value of the solution was adjusted to 10 with sodium bicarbonate (sat.), extracted with dichloromethane (100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied on a silica gel column and eluted with EtOAc/petroleum ether (1:1) to give 450 mg (80%) of 4-[[(3S)-3-(hydroxymethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexan-1-one as a yellow oil.

Workup

  1. extractionextracted with dichloromethane (100 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. washeluted with EtOAc/petroleum ether (1:1)

Sources & evidence

ORD record
ord-88d6514ad4ef4129856e25fa5e32483e
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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