Hydrochloric Acid → HCID 86708929, compound

HRID 1522081Notes

Reaction equation

HRID 1522081 reaction equation
C(O[N:5]1[CH2:10][CH:9]([CH3:11])[CH2:8][N:7]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=2[Cl:23])[S:6]1(=[O:25])=[O:24])(=O)C.[C:26]([O:29]CC)(=[O:28])[CH3:27].Cl>C1COCC1.CO.O>[Cl:18][C:17]1[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=[C:13]([Cl:23])[C:12]=1[N:7]1[S:6](=[O:24])(=[O:25])[N:5]([CH2:27][C:26]([OH:29])=[O:28])[CH2:10][CH:9]([CH3:11])[CH2:8]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86708930HCID 86708930, compound

Product 1

HCID 86708929HCID 86708929, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 2-(6-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-methyl-1,1-dioxido-1,2,6-thiadiazinan-2-yl acetate (220 mg, 0.45 mmol) in THF (10 mL) and MeOH (10 mL), was dropwisely added LiOH monohydrate (94 mg, 0.45 mmol) in water (3 mL) and agitated for 5 hr at room temperature. After addition of ethyl acetate (30 mL) and water (30 mL), pH of the resultant was adjusted to 3 with 1 N HCl and extracted to obtain the organic layer. The resultant was dried over MgSO4, concentrated under reduced pressure, and crystallized with ethyl acetate (1 mL) and hexane (10 mL), giving the compound of interest (163 mg, 86%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.67 (s, 1H), 7.64 (s, 1H), 4.53-4.47 (m, 1H), 4.12-3.91 (m, 3H), 3.46-3.42 (m, 1H), 3.26-3.19 (m, 1H), 2.59 (m, 1H), 0.96 (d, 3H, J=6.7 Hz).

Workup

  1. extractionextracted
  2. customto obtain the organic layer
  3. dry with materialThe resultant was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customcrystallized with ethyl acetate (1 mL) and hexane (10 mL)
  6. customgiving the compound of interest (163 mg, 86%, white solid)

Sources & evidence

ORD record
ord-613f70945e0b4d7c80ad3b30add6135d
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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