Hydrochloric Acid → HCID 59699472, compound

HRID 901077Notes

Reaction equation

HRID 901077 reaction equation
Cl.[F:2][CH2:3][C@@H:4]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH2:18][F:19])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[O:7]C(C)(C)[N:5]1C(OC(C)(C)C)=O>CO>[NH2:5][C@H:4]([CH2:3][F:2])[C@@H:8]([C:9]1[CH:10]=[CH:11][C:12]([S:15]([CH2:18][F:19])(=[O:17])=[O:16])=[CH:13][CH:14]=1)[OH:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68720375HCID 68720375, compound

Product 1

HCID 59699472HCID 59699472, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 6N HCl (30 ml, 5.5 eq ) was added to a solution of 16 (12.0 g) in 200 ml of MeOH at room temperature, and the reaction mixture was warmed up to 40° C. overnight. Methanol was removed in vacuo. The reaction mixture was washed with diethyl ether (50 ml×2). The aqueous solution was neutralized with 2N NaOH and extracted with ethyl acetate (100 ml×3). The organic layer was washed with brine, dried over sodium sulfate, and concentrated to provide the pure desired product (7.6 g).

Workup

  1. customMethanol was removed in vacuo
  2. washThe reaction mixture was washed with diethyl ether (50 ml×2)
  3. extractionextracted with ethyl acetate (100 ml×3)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-81b4142d37f648919e082a2ad448670f
Source dataset
uspto-grants-2008_04
Patent number
US07361689B2

Reaction notes

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