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

HRID 1796306Notes

Reaction equation

HRID 1796306 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-6f443ce55ea44fe4a4519f014f163900
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

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