4-Methoxyphenyl isothiocyanate → HCID 86654763, compound

HRID 447139Notes

Reaction equation

HRID 447139 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:16])[C@@H:6]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])[CH2:7][CH3:8].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1>ClCCl>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[S:27])[NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:16])[C@H:6]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:12])[F:13])[CH2:7][CH3:8])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 752934-Methoxyphenyl isothiocyanateHCID 86654760HCID 86654760, compound

Product 1

HCID 86654763HCID 86654763, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)—N-(2-aminoethyl)-2-(2,2,2-trifluoroacetamido)butanamide (276.6 mg, ca, 1.10 mmol) in dichloromethane (10 mL) was added 4-methoxyphenyl isothiocyanate (120 μL, 0.868 mmol). and the resulting mixture was stirred for 72 h at room temperature. The resulting mixture was then concentrated to an oil, which was purified by column chromatography, eluting with 6% methanol in chloroform to yield (R)—N-(2-(3-(4-methoxyphenyl)thioureido)ethyl)-2-(2,2,2-trifluoroacetamido)butanamide as a solid.

Workup

  1. concentrationThe resulting mixture was then concentrated to an oil, which
  2. customwas purified by column chromatography
  3. washeluting with 6% methanol in chloroform

Sources & evidence

ORD record
ord-e13e10009533462186199fd7c78f9da1
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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