Water → HCID 90272113, compound

HRID 1503893Notes

Reaction equation

HRID 1503893 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][C:12]=2[O:30][CH3:31])[C:3]=1[C:32](=[O:34])[NH2:33].Br[CH2:36][C:37](=O)[C:38]([O:40][CH2:41][CH3:42])=[O:39].O>C(O)(=O)C.CN(C)C=O>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:15]=[CH:16][C:11]([NH:10][C:4]3[N:5]=[C:6]([S:8][CH3:9])[N:7]4[CH:36]=[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:1]=[C:2]4[C:3]=3[C:32](=[O:34])[NH2:33])=[C:12]([O:30][CH3:31])[CH:13]=2)[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 3

HCID 962WaterHCID 66144Ethyl bromopyruvateHCID 90272088HCID 90272088, compound

Product 1

HCID 90272113HCID 90272113, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the product of Example 13D (1 g, 2.0 mmol), ethyl 3-bromo-2-oxopropanoate (796 mg, 4.1 mmol) and acetic acid (2 drops) in dimethylformamide (20 mL) was heated at 60° C. for 16 hours. After cooling to ambient temperature, the mixture was poured into water and extracted with dichloromethane (2×100 mL). The combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 98/2 dichloromethane/methanol to give the title compound. MS: 586 (M+H+).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with dichloromethane (2×100 mL)
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  8. washeluting with 98/2 dichloromethane/methanol

Sources & evidence

ORD record
ord-21141e52c36040be82ea5521a3ea9523
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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