Potassium trimethylsilanolate → Potassium 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoate

HRID 79506Notes

Reaction equation

HRID 79506 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:22]([CH3:24])[CH3:23])[CH2:9][CH:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:11]([O:13]C)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[O-].[K+:30]>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH:22]([CH3:24])[CH3:23])[CH2:9][CH:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:11]([O-:13])=[O:12])=[O:7])([CH3:3])([CH3:4])[CH3:2].[K+:30]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 66617968Methyl 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoate

Product 1

HCID 66617918Potassium 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoateYield 105%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoate (133 g, 374 mmol) was dissolved in THF (1.0 L) and treated with potassium trimethylsilanolate (“KOTMS”; 56.0 g, 392 mmol) at room temperature. The mixture was allowed to stir overnight to completion by LCMS analysis of the crude. The mixture was concentrated in vacuo to afford a wet foam, which was allowed to dry under vacuum overnight to afford potassium 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoate as a solid (148.7 g, 105%). LC/MS (APCI+) m/z 242.1 [M-Boc-K]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto afford a wet foam, which
  3. customto dry under vacuum overnight

Sources & evidence

ORD record
ord-1fa21d3c64e0460da7c0f87af620572c
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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