Sodium Bicarbonate → HCID 89463070, compound

HRID 1473250Notes

Reaction equation

HRID 1473250 reaction equation
[OH:1][CH:2]([C:7]1[N:12]([CH3:13])[C:11](=[O:14])[C:10]2[S:15][C:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:9]=2[C:8]=1[C:22]1[C:23]([CH3:32])=[C:24]2[C:29](=[CH:30][CH:31]=1)[O:28][CH2:27][CH2:26][CH2:25]2)[C:3]([O:5][CH3:6])=[O:4].C([O-])(O)=O.[Na+]>C(OC(C)(C)C)(=O)C>[CH3:6][O:5][C:3](=[O:4])[CH:2]([O:1][C:8]([CH3:22])([CH3:9])[CH3:7])[C:7]1[N:12]([CH3:13])[C:11](=[O:14])[C:10]2[S:15][C:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:9]=2[C:8]=1[C:22]1[C:23]([CH3:32])=[C:24]2[C:29](=[CH:30][CH:31]=1)[O:28][CH2:27][CH2:26][CH2:25]2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 89462741HCID 89462741, compound

Product 1

HCID 89463070HCID 89463070, compoundYield 118.9%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a solution of compound methyl 2-hydroxy-2-(2-methyl-4-(5-methylchroman-6-yl)-1-oxo-1,2,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-c]pyridin-3-yl)acetate (30 mg, 0.066 mmol) in t-Butyl acetate (3 mL) was added HClO4 (6.64 mg, 0.066 mmol). The mixture was stirred at room temperature for 30 min. The reaction mixture neutralized with saturated aqueous NaHCO3 (10 mL). The resulting solution was extracted with ethyl acetate (15 mL×3). The combined ethyl acetate were dried over Na2SO4 and concentrated to dryness to give crude product, which was purification with prep-TLC afford title product (20 mg, 59% yield) as a solid. LCMS (m/z) ES+=510 (M+1)

Workup

  1. extractionThe resulting solution was extracted with ethyl acetate (15 mL×3)
  2. dry with materialThe combined ethyl acetate were dried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customto give crude product, which
  5. custompurification

Sources & evidence

ORD record
ord-46291dd9a5a84752ba59824286ec46eb
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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