Stannous Chloride → HCID 86616426, compound

HRID 737153Notes

Reaction equation

HRID 737153 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:32])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl>CCO.CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:32])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 74316515HCID 74316515, compound

Product 1

HCID 86616426HCID 86616426, compound

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

500 mg (1.1 mmol) of 2-[4-(3-Nitro-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester was dissolved in 30 mL of 1:1 mixture of EtOH/EtOAc. To this solution was added SnCl2 (0.87 g, 3.9 mmol). Reaction mixture was heated under reflux for 5 hours. After 5 hours reaction mixture was cooled to room temperature and evaporated. It was redissolved in EtOAc (150 mL) and washed using sat. K2CO3. Organic phase was isolated, washed using brine and water and evaporated to dryness to give Compound 5001. MS: 422.1 (M+H+).

Workup

  1. customReaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 5 hours
  4. customAfter 5 hours reaction mixture
  5. customevaporated
  6. dissolutionIt was redissolved in EtOAc (150 mL)
  7. washwashed
  8. customOrganic phase was isolated
  9. washwashed
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-135e7c358ef4499c960ff44af5f2149b
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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