HCID 67504646, compound → HCID 66894526, compound

HRID 19331Notes

Reaction equation

HRID 19331 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[CH2:7][NH:8][C@H:9]([C:20]([O:22][CH3:23])=[O:21])[CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])C>C(#N)C>[CH3:23][O:22][C:20](=[O:21])[C@@H:9]([N:8]1[CH2:7][C:6]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[CH:5][C:4]1=[O:3])[CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15]

Participants

3

Reactant 1

HCID 67504646HCID 67504646, compound

Product 1

HCID 66894526HCID 66894526, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 4-[(S)-3-(t-butyl-dimethyl-silanyloxy)-1-methoxycarbonyl-propylamino]-3-(2-chloro-phenoxy)-but-2-enoic acid ethyl ester (495 mg, 1.02 mmol) in acetonitrile (4 mL) was placed in a sealed microwave reaction tube and heated in a microwave reactor at 140° C. for 3 h. After this time, the mixture was cooled to room temperature and concentrated in vacuo with silica gel (2 g). Purification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded (S)-4-(t-butyl-dimethyl-silanyloxy)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-butyric acid methyl ester (255 mg, 49% over two steps) as a golden oil: HR-ES-MS m/z calculated for C21H30NO5ClSi [M+Na]+ 462.1474, observed 462.1473.

Workup

  1. temperatureAfter this time, the mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo with silica gel (2 g)
  3. customPurification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-93cc70bbcb3e40058678bfa990dd4fa1
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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