Sodium Bicarbonate → HCID 70236756, compound

HRID 1948171Notes

Reaction equation

HRID 1948171 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[NH:10][CH:11]([C:14]1([CH3:24])[CH2:23][CH2:22][C:17]2(OCC[O:18]2)[CH2:16][CH2:15]1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CC(C)=O.Cl>[CH2:1]([O:8][C:9](=[O:25])[NH:10][CH:11]([C:14]1([CH3:24])[CH2:15][CH2:16][C:17](=[O:18])[CH2:22][CH2:23]1)[CH2:12][CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58380824HCID 58380824, compound

Product 1

HCID 70236756HCID 70236756, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

5.50 g of [1-(8-methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-propyl]-carbamic acid benzyl ester (77) were dissolved in 15 mL of a 2:1 mixture of acetone and 6N aqueous hydrochloric acid. The reaction mixture was stirred for 16 h at room temperature, then dropped into 150 mL of saturated aqueous sodium bicarbonate solution. The mixture was extracted three times with dichloromethane (100 mL each), the combined organic phases were dried over magnesium sulphate, filtered and concentrated to give the ketone 78, which was used directly in the next step. Rt=0.59 min (Method P). Detected mass: 304.2 (M+H+).

Workup

  1. extractionThe mixture was extracted three times with dichloromethane (100 mL each)
  2. dry with materialthe combined organic phases were dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-197bf05cc8bf4403b44af19cda550913
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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