Ethyl bromoacetate → HCID 131727108, compound

HRID 2116613Notes

Reaction equation

HRID 2116613 reaction equation
[O:1]=[C:2]1[N:8]2[CH2:9][C@H:4]([C:5]3[CH:16]=[N:15][NH:14][C:6]=3[C@H:7]2[C:10]([O:12][CH3:13])=[O:11])[N:3]1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].CCN(C(C)C)C(C)C>C(#N)C>[CH3:13][O:12][C:10]([C@@H:7]1[C:6]2[N:14]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:15]=[CH:16][C:5]=2[C@H:4]2[CH2:9][N:8]1[C:2](=[O:1])[N:3]2[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:11]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 131727109HCID 131727109, compound

Product 1

HCID 131727108HCID 131727108, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

0.2 g of the product obtained in Stage K of Example 1 is dissolved in 2 ml of acetonitrile, in a round-bottomed flask. 0.150 μl of ethyl bromoacetate and 240 μl of DIEA are added. The medium is heated at 50° C. for 24 hours and then the reaction medium is extracted with ethyl acetate, the organic phase is washed with an aqueous tartaric acid solution at 10% and then with an aqueous NaCl solution. The organic phase is dried over magnesium sulfate, filtered off and the solvent is evaporated off under reduced pressure. 266 mg of the crude product are obtained which are purified by chromatography on silica, eluting with a methylene chloride/acetone/triethylamine, 95/0.5/0.1%, mixture. 37 mg of the isomer A, ethyl trans-4,5,6,8-tetrahydro-8-(methoxycarbonyl)-6-oxo-5-(phenylmethoxy)-1H-4,7-methanopyrazolo[3,4-e][1,3]diazepine-1-acetate having the empirical formula C20H22N4O6 are obtained (M=414.42 g).

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washthe organic phase is washed with an aqueous tartaric acid solution at 10%
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered off
  5. customthe solvent is evaporated off under reduced pressure
  6. custom266 mg of the crude product are obtained which
  7. customare purified by chromatography on silica
  8. washeluting with a methylene chloride/acetone/triethylamine, 95/0.5/0.1%, mixture

Sources & evidence

ORD record
ord-af95a5b821ad4ebdacbc8fbe5ea48d6f
Source dataset
uspto-grants-2008_10
Patent number
US07439253B2

Reaction notes

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