Sulfuric Acid → HCID 59734932, compound

HRID 881690Notes

Reaction equation

HRID 881690 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[C@H:14]1[CH2:20][N:19]2[C:21]([C:24]([O:27]C)([CH3:26])[CH3:25])=[CH:22][N:23]=[C:18]2[C@H:17]([NH:29]C(=O)OC(C)(C)C)[CH2:16][CH2:15]1>O>[NH2:29][C@@H:17]1[CH2:16][CH2:15][C@@H:14]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([F:13])[C:7]=2[F:6])[CH2:20][N:19]2[C:21]([C:24]([OH:27])([CH3:25])[CH3:26])=[CH:22][N:23]=[C:18]12

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86620139HCID 86620139, compound

Product 1

HCID 59734932HCID 59734932, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Concentrated sulfuric acid (0.335 mL, 5.70 mmol) was added to a solution of tert-butyl [(6S,9R)-6-(2,3-difluorophenyl)-3-(1-methoxy-1-methylethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-yl]carbamate (310 mg, 0.712 mmol) in H2O (2 mL) and the mixture heated to 60° C. After 2.5 h, the reaction mixture was quenched with saturated aqueous NaHCO3. The mixture was extracted with CH2Cl2 (3×), and the combined organic extracts were washed with water, saturated brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound. MS: m/z=322 (M+1).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NaHCO3
  2. extractionThe mixture was extracted with CH2Cl2 (3×)
  3. washthe combined organic extracts were washed with water, saturated brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce09778cfd914fe7b0f30ad467357fc7
Source dataset
uspto-grants-2015_03
Patent number
US08993588B2

Reaction notes

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