Tert-butyl 3-(2-(methoxycarbonyl)aminoethoxy)-3-(3-chlorophenyl)propyl(methyl)carbamate → Methyl 2-(1-(3-chlorophenyl)-3-(methylamino)propoxy)ethylcarbamate

HRID 426038Notes

Reaction equation

HRID 426038 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH2:6][CH2:7][O:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[CH2:10][CH2:11][N:12](C)[C:13](=O)OC(C)(C)C)=[O:4]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:27][C:23]1[CH:22]=[C:21]([CH:9]([O:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[O:2][CH3:1])[CH2:10][CH2:11][NH:12][CH3:13])[CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 1

HCID 66704353Tert-butyl 3-(2-(methoxycarbonyl)aminoethoxy)-3-(3-chlorophenyl)propyl(methyl)carbamate

Product 1

HCID 59364348Methyl 2-(1-(3-chlorophenyl)-3-(methylamino)propoxy)ethylcarbamateYield 199.9%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl 3-(2-(methoxycarbonyl)aminoethoxy)-3-(3-chlorophenyl)propyl(methyl)carbamate (100 mg) was dissolved in a solution of 20% (V/V) TFA/CH2Cl2 (8 mL). The reaction mixture was stirred at room temperature for 1 h, then concentrated in vacuo to afford methyl 2-(1-(3-chlorophenyl)-3-(methylamino)propoxy)ethylcarbamate (150 mg, 100%), was used for the next step without purification.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c802ecc19df146c99a27a550260b1b1f
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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