Hydrochloric Acid → HCID 66756845, compound

HRID 1642621Notes

Reaction equation

HRID 1642621 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][C:20](=[O:22])[NH:19][S:18]3(=[O:24])=[O:23])=[C:13]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:12]=2)[CH:5]=1.[Li+].[OH-].Cl>C1COCC1.O>[CH2:26]([O:25][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[N:17]1[CH2:21][C:20](=[O:22])[NH:19][S:18]1(=[O:23])=[O:24])[CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:33])=[O:2])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66757157HCID 66757157, compound

Product 1

HCID 66756845HCID 66756845, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-benzoic acid methyl ester (intermediate from Example LBY596) (0.3 g, 0.643 mmol) in THF is added a solution of LiOH (0.081 g, 1.929 mmol) in H2O. The reaction is stirred at ambient temperature overnight. The mixture is poured into 1 M HCl and extracted with EtOAc. The organic layer is dried over MgSO4, filtered and concentrated to afford a brown oil. The oil is place under high vacuum to afford solid 3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-benzoic acid: MS (M−H)−=451.2.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a brown oil

Sources & evidence

ORD record
ord-6b249398dd634b25813472fbe935c6ca
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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