Hydrochloric Acid → HCID 178461507, compound

HRID 245540Notes

Reaction equation

HRID 245540 reaction equation
C(=O)([O:7][CH:8]1[C:12]2[CH:13]=[C:14]([CH:26]=[O:27])[C:15]([N:18]3[CH2:23][C@H:22]([CH3:24])[O:21][C@H:20]([CH3:25])[CH2:19]3)=[C:16]([F:17])[C:11]=2[O:10][NH:9]1)OC(C)(C)C.Cl>CO>[CH3:25][C@H:20]1[O:21][C@@H:22]([CH3:24])[CH2:23][N:18]([C:15]2[C:14]([CH:26]=[O:27])=[CH:13][C:12]3[C:8]([OH:7])=[N:9][O:10][C:11]=3[C:16]=2[F:17])[CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86658132HCID 86658132, compound2×

Product 1

HCID 178461507HCID 178461507, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of tert-butyl 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-5-formyl-2,3-dihydro-1,2-benzisoxazol-3-yl carbonate (Intermediate 533, 0.5 g, 1.2 mmol) in methanol (5 ml) was added 5 ml of 5% aqueous HCl before heating at 75° C. for 2 hours. The reaction mixture was quenched with 10% aqueous sodium bicarbonate solution and extracted with EtOAc. The organic layer were washed with water, dried (sodium sulfate), and concentrated. The residue purified over a silica gel flash column (elution with 50-70% EtOAc in hexanes) to give product.

Workup

  1. customThe reaction mixture was quenched with 10% aqueous sodium bicarbonate solution
  2. extractionextracted with EtOAc
  3. washThe organic layer were washed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe residue purified over a silica gel flash column (elution with 50-70% EtOAc in hexanes)
  7. customto give product

Sources & evidence

ORD record
ord-0c2e9c7757c1473e8a96ef6d128d2ccb
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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