Water → HCID 25096412, compound

HRID 1926940Notes

Reaction equation

HRID 1926940 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([O:18][C@H:19]([CH3:23])[C@H:20]([OH:22])[CH3:21])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:5][CH:4]=1.[C:30]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])(=[O:33])[CH:31]=[CH2:32].O>C1COCC1>[C:35]([O:34][C:30](=[O:33])[CH2:31][CH2:32][O:22][C@H:20]([CH3:21])[C@H:19]([O:18][C:16]1[C:17]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[C:10]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:11][C:12]=2[N:13]=[CH:14][N:15]=1)[CH3:23])([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 962WaterHCID 15458tert-Butyl acrylateHCID 58016784HCID 58016784, compound

Product 1

HCID 25096412HCID 25096412, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 157 mg (1.37 mmol) potassium tert.-butylate to a solution of 535 mg (1.37 mmol) (2R,3R)-3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}butan-2-ol in 5 ml THF. After stirring for 15 min at RT, add 1.0 ml (878 mg, 6.65 mmol) tert.-butyl acrylate. After three hours, add 10 ml water, and concentrate the reaction mixture by vacuum evaporation. Purify the residue by preparative RP-HPLC (gradient: water/acetonitrile). 346 mg (47% of theor.) of the desired product is obtained.

Workup

  1. waitAfter three hours
  2. concentrationconcentrate the reaction mixture
  3. customby vacuum evaporation
  4. customPurify the residue by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-079b502d2ddc44ec867a497864e00b70
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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