Water → HCID 69491568, compound

HRID 1296763Notes

Reaction equation

HRID 1296763 reaction equation
[NH2:1][C:2]1[CH:16]=[C:15]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)[CH:14]=[CH:13][C:3]=1[CH2:4]NC(=O)OC(C)(C)C.[C:23](=[O:26])([O-:25])[O-].[K+].[K+].[CH2:29]([O:36][C:37](=[O:40])[CH2:38]Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CN(C=O)C>[C:3]([O:25][C:23]([CH2:4][C:3]1[CH:13]=[CH:14][C:15]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[CH:16][C:2]=1[NH:1][CH2:38][C:37]([O:36][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:40])=[O:26])([CH3:13])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 86595903HCID 86595903, compound

Product 1

HCID 69491568HCID 69491568, compoundYield 165.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of compound 58b (0.57 g, 1.88 mmol) and potassium carbonate (0.519 g, 3.76 mmol) in DMF (6 mL) in a pressure tube was added benzyl-2-bromoacetate (0.447 mL, 2.8 mmol). The reaction mixture was heated at 80° C. overnight, then cooled to rt. Water was added, and the mixture was extracted with ethyl acetate (3×). The combined organics were washed with water and brine, dried, and concentrated. The residue was purified by silica gel chromatography using a gradient from 10 to 30% ethyl acetate in hexanes to give compound 58c (0.68 g, 80%) as a clear oil. ESI-MS m/e 453.5 (M+1).

Workup

  1. temperaturecooled to rt
  2. extractionthe mixture was extracted with ethyl acetate (3×)
  3. washThe combined organics were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-62feea5f63144d5c8d562d276bd37e63
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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