Lithium Hydroxide → HCID 70683867, compound

HRID 1522063Notes

Reaction equation

HRID 1522063 reaction equation
[O:1]=[S:2]1(=[O:20])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:14][C:15]([O:17]CC)=[O:16].[Li+].[OH-]>C1COCC1.CO.O>[O:20]=[S:2]1(=[O:1])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86708911HCID 86708911, compound

Product 1

HCID 70683867HCID 70683867, compoundYield 97.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 2-(1,1-dioxido-6-phenyl-1,2,6-thiadiazinan-2-yl)acetate (260 mg, 0.872 mmol) in THF (5 mL) and MeOH (5 mL), was added LiOH (182.9 mg, 4.36 mmol) in H2O (5 mL). The reaction mixture was agitated for 3 hr at room temperature and evaporated. The residue was introduced into ice water, its pH was adjusted down to 1 with 2 N HCl, and extracted with ethyl acetate. The organic layer was dried over MgSO4 to give 2-(1,1-dioxido-6-phenyl-1,2,6-thiadiazinan-2-yl)acetic acid (230 mg, 97%, yellow solid). 1H NMR (300 MHz, DMSO-d6): δ 12.81 (s, 1H), 7.43-7.26 (m, 5H), 3.96 (s, 2H), 3.68-3.62 (m, 4H), 1.92-1.85 (m, 2H).

Workup

  1. customevaporated
  2. additionThe residue was introduced into ice water, its pH
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4

Sources & evidence

ORD record
ord-76a7a4bd35ac47e8831cfbb7a7a45795
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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