Hydrochloric Acid → HCID 86708921, compound

HRID 1522073Notes

Reaction equation

HRID 1522073 reaction equation
[O:1]=[S:2]1(=[O:25])[N:9]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[Cl:18])[CH2:8][C:5]2([CH2:7][CH2:6]2)[CH2:4][N:3]1[CH2:19][C:20]([O:22]CC)=[O:21].C(OCC)(=O)C.Cl>C1COCC1.CO.O>[O:25]=[S:2]1(=[O:1])[N:9]([C:10]2[C:11]([Cl:18])=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=2[Cl:16])[CH2:8][C:5]2([CH2:6][CH2:7]2)[CH2:4][N:3]1[CH2:19][C:20]([OH:22])=[O:21]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86708920HCID 86708920, compound

Product 1

HCID 86708921HCID 86708921, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 2-(6,6-dioxido-7-(2,4,6-trichlorophenyl)-6-thia-5,7-diazaspiro[2,5]-octane-5-yl)acetate (60 mg, 0.14 mmol) in THF (5 mL) and MeOH (5 mL), was added LiOH monohydrate (25 mg, 0.58 mmol) in water (1 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 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 (50 mg, 89%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.39 (s, 2H), 4.39 (s, 2H), 3.73 (s, 2H), 3.57 (s, 2H), 0.66-0.64 (m, 4H).

Workup

  1. extractionextracted to the organic layer
  2. dry with materialThe resultant was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customcrystallized with ethyl acetate (1 mL) and hexane (10 mL)
  5. customgiving the compound of interest (50 mg, 89%, white solid)

Sources & evidence

ORD record
ord-6d2806e3aa7e4d9fbd0d9aac03d26591
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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