1,4-Dioxane hydrochloride → [2-Amino-2-(3-bromo-phenyl)-3,3,3-trifluoro-propoxy]-acetic acid ethyl ester

HRID 2196238Notes

Reaction equation

HRID 2196238 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][O:6][CH2:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=1)([NH:13]C(OC(C)(C)C)=O)[C:9]([F:12])([F:11])[F:10])[CH3:2].Cl.O1CCOCC1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][O:6][CH2:7][C:8]([NH2:13])([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=1)[C:9]([F:10])([F:12])[F:11])[CH3:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66666311[2-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-3,3,3-trifluoro-propoxy]-acetic acid ethyl ester

Product 1

HCID 66666183[2-Amino-2-(3-bromo-phenyl)-3,3,3-trifluoro-propoxy]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.4 g (2.47 mmol) [2-(3-bromo-phenyl)-2-tert-butoxycarbonylamino-3,3,3-trifluoro-propoxy]-acetic acid ethyl ester in 5 ml DCM was treated with 3.74 ml 4N HCl/dioxane. After standing overnight the mixture was evaporated, taken up in EtOAc and washed with 10% aqueous NaHCO3. The organic phase was washed with brine, dried with Na2SO4 and purified via chromatography on silica gel (c-hexane/10-15% EtOAc) to give the desired product as a colorless resin.

Workup

  1. customthe mixture was evaporated
  2. washwashed with 10% aqueous NaHCO3
  3. washThe organic phase was washed with brine
  4. dry with materialdried with Na2SO4
  5. custompurified via chromatography on silica gel (c-hexane/10-15% EtOAc)

Sources & evidence

ORD record
ord-5c640e5683034e5ea70b89bc423b4689
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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