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

HRID 532769Notes

Reaction equation

HRID 532769 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].O([Si](C)(C)C)[K:26]>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+:26]

Participants

4

Reactant 2

HCID 66617968Methyl 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoateHCID 178504318HCID 178504318, compound

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 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 white 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-c3c6e5ec8ccd43d9a84b213e6cf686a6
Source dataset
uspto-grants-2014_10
Patent number
US08853199B2

Reaction notes

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