Hydrochloric Acid → HCID 90449936, compound

HRID 1411257Notes

Reaction equation

HRID 1411257 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:19](=[O:36])[NH:20][C:21]3[S:22][C:23]([S:26][CH2:27][CH2:28][O:29]C4CCCCO4)=[CH:24][N:25]=3)[C:5]2=[CH:6][CH:7]=1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:19](=[O:36])[NH:20][C:21]3[S:22][C:23]([S:26][CH2:27][CH2:28][OH:29])=[CH:24][N:25]=3)[C:5]2=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90449586HCID 90449586, compound

Product 1

HCID 90449936HCID 90449936, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The methyl 5-chloro-1-((5-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)thio)thiazol-2-yl)carbamoyl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (90.0 mg, 0.163 mmol) obtained in Example 136 was dissolved in tetrahydrofuran (1 mL) and methanol (1 mL). Thereafter, a 12 N aqueous solution of hydrochloric acid (0.2 mL) was added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 10 minutes. Thereafter, the reaction solution was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (63.0 mg, 82%) in the form of a white solid.

Workup

  1. extractionwas then extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-02b3ddeb6c82406a98f13b95ecf442b5
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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