Ethyl bromoacetate → HCID 70846803, compound

HRID 1972198Notes

Reaction equation

HRID 1972198 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(#N)C>[CH2:30]([O:29][C:27]([CH2:26][O:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 66763747Tert-butyl (S)-(1-(3-fluorophenyl)-2-hydroxyethyl)carbamate

Product 1

HCID 70846803HCID 70846803, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Tert-butyl (S)-1-(3-fluorophenyl)-2-hydroxyethylcarbamate (256 mg, 1.0 mmol) was dissolved in acetonitrile (10 mL) and treated with cesium carbonate (391 mg, 1.2 mmol) and ethyl bromoacetate (0.14 mL, 1.25 mmol). The mixture was heated to 100° C. for 30 min, then cooled to room temperature, acidified, and extracted with ethyl acetate. Purification on silica gel (15%-40% ethyl acetate/hexanes) gave 69 mg of tert-butyl (S)-2-((ethoxycarbonyl)methoxy)-1-(3-fluorophenyl)ethylcarbamate as a colorless glass. HPLC-MS calculated for C17H24FNO5 (M+H+) 342.2, found 342.1.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. customPurification on silica gel (15%-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ad96e758afa54211b3f07ac9344cb542
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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