Hydrochloric Acid → HCID 70220203, compound

HRID 473112Notes

Reaction equation

HRID 473112 reaction equation
[CH3:1][CH:2]([S:4]([NH:7][C@@H:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=2)[CH2:9]1)(=[O:6])=[O:5])[CH3:3].[OH-].[Li+].CCOC(C)=O.Cl>O.CO>[CH3:3][CH:2]([S:4]([NH:7][C@@H:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=2)[CH2:9]1)(=[O:6])=[O:5])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 66733844(S)-methyl 2-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 70220203HCID 70220203, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of (S)-methyl 2-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (2.320 mmol, 690 mg) and lithium hydroxide (5.10 mmol, 122 mg) in H2O (25 mL) and MeOH (25 mL) was stirred at room temp for 2 days. EtOAc was added followed by 2M aq HCl and the reaction mixture extracted with EtOAc (×3). The EtOAc layers were combined and washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo to give desired product as a white solid (514 mg, 78%). MS (ESI): m/z [M−H]− 282.2

Workup

  1. extractionthe reaction mixture extracted with EtOAc (×3)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c40b9c0fdd1a4568a457c71355560854
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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