Acetic Anhydride → HCID 53642917, compound

HRID 728679Notes

Reaction equation

HRID 728679 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[CH:12][C:13]([NH:32][CH3:33])=[C:14]([C:16](=[N:30][OH:31])[CH2:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=3[O:28][CH3:29])[CH:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>CN(C)C1C=CN=CC=1.ClCCl>[C:34]([O:31][N:30]=[C:16]([C:14]1[CH:15]=[C:10]([C:8](=[O:9])[NH:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:11]=[CH:12][C:13]=1[NH:32][CH3:33])[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1[O:28][CH3:29])(=[O:36])[CH3:35]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 73654802HCID 73654802, compound

Product 1

HCID 53642917HCID 53642917, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 4-[2-[5-(N-cyclopentylmethylcarbamoyl)-2-methylaminophenyl]-2-(hydroxyimino)ethyl]-3-methoxybenzoate (79.9 mg), 4-(dimethylamino)pyridine (22mg), and acetic anhydride (0.17 ml) in dichloromethane (11 ml) was stirred under a nitrogen atmosphere for 15 hours. The solution was diluted with dichloromethane, washed with 5% w/v sodium hydrogen sulfate, water, and brine, then dried (MgSO4), and evaporated to give methyl 4-[2-(acetoxyimino)-2-[5-(N-cyclopentylmethylcarbamoyl)-2-methylaminophenyl]ethyl]-3-methoxybenzoate (74.1 mg, 85%) as a pink solid; NMR (80 MHz, CDCl3): 1.2-1.8 [8H, (CH2)4 ], 2.1 (s, 3H, CH3CO), 3.0 (d, 3H, NCH3), 3.3 (dd, 2H, CH2NH), 3.9 (2s, 6H, 2×OCH3), 4.3(s, 2H, ArCH2), 5.8 (broad, 1H, NHCO), 6.7(d, 1H), 7.0 (d, 1H), 7.4-7.6 (m, 3H), 7.8 (d, 1H), 8.5 (broad, 1H, CH3NH).

Workup

  1. washwashed with 5% w/v sodium hydrogen sulfate, water, and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-00fcb054a7ca47e09da8ef2b1300b835
Source dataset
uspto-grants-1991_09
Patent number
US05049679

Reaction notes

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