Hydrochloric Acid → HCID 69953870, compound

HRID 1266467Notes

Reaction equation

HRID 1266467 reaction equation
C[O:2][C:3](=[O:18])[C:4]([OH:17])=[CH:5][C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15].[OH-].[Na+].CO.Cl>CCOC(C)=O>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:6](=[O:16])[CH:5]=[C:4]([OH:17])[C:3]([OH:18])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 69953686HCID 69953686, compound

Product 1

HCID 69953870HCID 69953870, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Intermediate 1B (320 mg, 1.2 mmol) was treated with 1.31 ml of 1 N NaOH, a small amount of MeOH was added to aid dissolution of the ester. The resulting suspension was stirred for 2 h then acidified with 1N HCl and EtOAc was added. The organic layer was separated, washed with brine, dried over Na2SO4 then filtered and the solvent removed to yield 240 mg oil. The crude product was purified by reverse phase preparative HPLC (C18, MeOH/H2O (0.1% TFA)-gradient). MS (M−H) calcd for C12H10NO4Cl: 253.0268; found: 253.0267.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationthen filtered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-230541a0d2da482b8ba3cab191173754
Source dataset
uspto-grants-2003_04
Patent number
US06548546B2

Reaction notes

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