Hydrochloric Acid → HCID 69057447, compound

HRID 2100573Notes

Reaction equation

HRID 2100573 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=2[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH:10]([C:29](N2C3CC4C(C)(C)C3(CC4)CS2(=O)=O)=[O:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:45].[Li+].Cl>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[C:14]=2[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[C@@H:10]([C:29]([OH:30])=[O:45])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69056491HCID 69056491, compound

Product 1

HCID 69057447HCID 69057447, compoundYield 138.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 3-(10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-4-(2-isopropoxycarbonyl-3-trifluoromethyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (625 mg, 0.97 mmol)) in 20 mL of 2:1 THF/H2O was added lithium hydroxide (70 mg, 2.91 mmol). The reaction mixture was allowed to stir at ambient temperature for 18 h. The reaction was acidified with 1 N HCl and extracted with EtOAc. The EtOAc layer was washed with brine, dried (MgSO4) and concentrated to afford 0.60 g of a mixture of the title compound and (1R)-(+)-2,10-camphorsultam, which was used without purification. LRMS (ES)+: 446.28 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4a2f00bc2e674ab5bfbc7740688b3924
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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