Acetic Anhydride → HCID 86609466, compound

HRID 1171728Notes

Reaction equation

HRID 1171728 reaction equation
[ClH:1].[C:2]([CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1/[CH:11]=[C:12]1\[CH2:13][N:14]([CH:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[C:20]([CH:22]2[CH2:24][CH2:23]2)=[O:21])[CH2:15][CH2:16][CH:17]\1[SH:18])([OH:4])=[O:3].C(N(CC)CC)C.[C:39](OC(=O)C)(=[O:41])[CH3:40]>ClCCl>[ClH:1].[C:39]([S:18][CH:17]1[CH2:16][CH2:15][N:14]([CH:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[C:20]([CH:22]2[CH2:23][CH2:24]2)=[O:21])[CH2:13]/[C:12]/1=[CH:11]\[C:7]1[N:6]([CH2:5][C:2]([OH:4])=[O:3])[CH:10]=[CH:9][N:8]=1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23138682HCID 23138682, compound

Product 1

HCID 86609466HCID 86609466, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-3-{[1-(carboxymethyl)-1H-imidazol-2-yl]methylidene}-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidine hydrochloride (85.6 mg) in dichloromethane (4 ml) were added triethylamine (120 μl) and acetic anhydride (80 μl) at 0° C. After the mixture was stirred at room temperature for 3 hours, solvents were removed under reduced pressure and the residue was purified by silica gel chromatography using methanol and dichloromethane (5:95 to 25:75) as eluents to afford the free base of the title compound (57.7 mg, yield: 71%) as a colourless oil.

Workup

  1. customsolvents were removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9a518afa87ab486593c3022e97d7e5ad
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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