Dimethylformamide → HCID 86613202, compound

HRID 2375511Notes

Reaction equation

HRID 2375511 reaction equation
C(N[O:5][C:6]1[CH2:7][CH2:8][C:9]2[CH2:10][C@H:11]3[N:23]([CH3:24])[CH2:22][CH2:21][C@:17]45[C:18]=2[C:19]=1[O:20][C@H:16]4[C@@H:15]([OH:25])[CH:14]=[CH:13][C@@H:12]35)(=O)C.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:34](=O)([O-])[O-].[K+].[K+].C[N:41]([CH:43]=[O:44])C>>[C:43]([NH:41][C@:15]1([OH:25])[CH:14]=[CH:13][C@@H:12]2[C@:17]34[CH2:21][CH2:22][N:23]([CH3:24])[C@@H:11]2[CH2:10][C:9]2[CH2:8][CH2:7][C:6]([O:5][CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[C:19]([O:20][C@@H:16]13)[C:18]4=2)(=[O:44])[CH3:34]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86613203HCID 86613203, compound

Product 1

HCID 86613202HCID 86613202, compound

Conditions

Temperature
60 °C

Procedure

To 500 mg (1.52 mmol) of 6 is added 12 mL of anhydrous DMF followed by 270 μL (2.26 mmol) of benzyl bromide and 734 mg (5.3 mmol) of anhydrous potassium carbonate. The reaction mixture is allowed to heat at 60° C. for 18 h, then is cooled to room temperature and filtered. The filtrate is concentrated and purified by preparative RP-HPLC using using a gradient run with acetonitrile-water containing 0.1% trifluoroacetic acid. Fractions containing the desired product are combined and concentrated followed by lyophilization to give 26.

Workup

  1. temperatureis cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated
  4. custompurified by preparative RP-HPLC
  5. additionFractions containing the desired product
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a8dde14c941343ac89797877c947397c
Source dataset
uspto-grants-2008_12
Patent number
US07465797B2

Reaction notes

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