Acetic Anhydride → HCID 52932008, compound

HRID 1626785Notes

Reaction equation

HRID 1626785 reaction equation
[OH:1][C:2]1[C:3]([C:30]([NH:32][CH2:33][C:34]([OH:36])=[O:35])=[O:31])=[N:4][C:5]([CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=4)=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[N:6][C:7]=1[CH3:8].[C:37](OC(=O)C)(=[O:39])[CH3:38].C(N(CC)CC)C>C(#N)C.CN(C)C1C=CN=CC=1>[C:37]([O:29][CH2:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]2[CH:18]=[CH:17][C:16]([N:13]3[CH2:14][CH2:15][CH:10]([CH2:9][C:5]4[N:4]=[C:3]([C:30]([NH:32][CH2:33][C:34]([OH:36])=[O:35])=[O:31])[C:2]([OH:1])=[C:7]([CH3:8])[N:6]=4)[CH2:11][CH2:12]3)=[CH:21][CH:20]=2)=[CH:23][CH:24]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 52937955HCID 52937955, compound

Product 1

HCID 52932008HCID 52932008, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

({[5-Hydroxy-2-{(1-[4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid (0.13 g, 0.27 mmol) was dissolved in acetonitrile (8 mL), and acetic anhydride (0.063 mL, 0.67 mmol), triethylamine (0.092 mL, 0.66 mmol) and 4-dimethylaminopyridine (0.081 g, 0.66 mmol) were added, followed by stirring at room temperature for 3 hours. After the reaction solution was concentrated under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: dichloromethane/methanol), and a fraction corresponding to the Rf value=0.20 (dichloromethane/methanol=9/1) by thin layer chromatography was concentrated under reduced pressure. A mixed solvent of ethanol and water was added to the residue, whereby a solid was deposited. The resulting solid was collected by filtration, and dried under reduced pressure to afford the title compound (0.070 g, 0.13 mmol) as a pale yellowish white solid (yield 50%).

Workup

  1. concentrationAfter the reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: dichloromethane/methanol)
  3. concentrationa fraction corresponding to the Rf value=0.20 (dichloromethane/methanol=9/1) by thin layer chromatography was concentrated under reduced pressure
  4. additionA mixed solvent of ethanol and water was added to the residue, whereby a solid
  5. filtrationThe resulting solid was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4d873663fc7947bf8be0f8e2c4287c00
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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