Acetic Anhydride → HCID 68196369, compound

HRID 1626800Notes

Reaction equation

HRID 1626800 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:38]([NH:40][CH2:41][C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])=[O:39])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([CH:35]([OH:37])[CH3:36])=[CH:31][N:30]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:52](OC(=O)C)(=[O:54])[CH3:53].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl.N1C=CC=CC=1>[C:52]([O:37][CH:35]([C:32]1[CH:33]=[CH:34][C:29]([C:26]2[CH:27]=[CH:28][C:23]([N:20]3[CH2:19][CH2:18][CH:17]([CH2:16][C:12]4[N:11]=[C:10]([C:38]([NH:40][CH2:41][C:42]([O:44][CH2:45][C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)=[O:43])=[O:39])[C:9]([O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[C:14]([CH3:15])[N:13]=4)[CH2:22][CH2:21]3)=[CH:24][CH:25]=2)=[N:30][CH:31]=1)[CH3:36])(=[O:54])[CH3:53]

Participants

7

Reactant 4

HCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 68196368HCID 68196368, compound

Product 1

HCID 68196369HCID 68196369, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Benzyl [({5-(benzyloxy)-2-[(1-{4-[5-(1-hydroxyethyl)pyridin-2-yl]phenyl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetate (0.24 g, 0.35 mmol) obtained in Example 12-(3) was dissolved in dichloromethane (30 mL), and acetic anhydride (0.050 mL, 0.52 mmol) and triethylamine (1.8 mL) were added, followed by stirring at room temperature for 12 hours. Acetic anhydride (1.8 mL) and pyridine (0.90 mL) were added to the reaction solution, followed by stirring for further 12 hours, and subsequently a saturated aqueous sodium hydrogencarbonate solution was added, followed by extraction with ethyl acetate. After the organic layer was concentrated under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.12 g, 0.17 mmol) as a yellow oil (yield 48%).

Workup

  1. stirringby stirring for further 12 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. concentrationAfter the organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  5. concentrationa fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-beaab99df6fe4c6aa29115e3e69c8c64
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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