Potassium trimethylsilanolate → (2R,4R)-4-{[1-(4-Chloro-phenylcarbamoyl)-4-methoxy-pyrrolidine-2-carbonyl]-amino}-benzoic acid

HRID 2217589Notes

Reaction equation

HRID 2217589 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C@H:13]2[CH2:17][C@@H:16]([O:18][CH3:19])[CH2:15][N:14]2[C:20](=[O:29])[NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[O:12])=[CH:6][CH:5]=1.C[Si](C)(C)[O-].[K+]>C1COCC1>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:20]([N:14]2[CH2:15][C@H:16]([O:18][CH3:19])[CH2:17][C@@H:13]2[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:30])=[O:2])=[CH:5][CH:6]=2)=[O:12])=[O:29])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 68807390(2R,4R)-4-{[1-(4-Chloro-phenylcarbamoyl)-4-methoxy-pyrrolidine-2-carbonyl]-amino}-benzoic acid methyl ester

Product 1

HCID 68806708(2R,4R)-4-{[1-(4-Chloro-phenylcarbamoyl)-4-methoxy-pyrrolidine-2-carbonyl]-amino}-benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 9 (3.0 g, 6.94 mmol) in THF (50 mL) was added potassium trimethylsilanolate (3.85 g, 27.3 mmol). The solution was stirred at RT for 48 h before concentrating under reduced pressure and adding EtOAc. The solution was washed sequentially with 1N HCl, and brine, before drying over MgSO4 and concentrating under reduced pressure to give 10 (2.9 g, 100%). MS: APCI (AP+): 418.1 (M)+, (AP−): 416.1 (M)−

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. additionadding EtOAc
  3. washThe solution was washed sequentially with 1N HCl, and brine
  4. dry with materialbefore drying over MgSO4
  5. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-f6527bc8ffde4d5b968d26b8267197d4
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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