Acetic Acid → HCID 178476700, compound

HRID 2110109Notes

Reaction equation

HRID 2110109 reaction equation
[OH:1][NH:2][C:3]([C:5]1[O:9][C:8]([C:10]2[O:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21](=[NH:24])[NH:22][OH:23])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)=[CH:7][CH:6]=1)=[NH:4].[C:25](OC(=O)C)(=[O:27])[CH3:26].[C:32](O)(=[O:34])[CH3:33]>>[C:25]([O:1][NH:2][C:3]([C:5]1[O:9][C:8]([C:10]2[O:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21](=[NH:24])[NH:22][O:23][C:32](=[O:34])[CH3:33])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)=[CH:7][CH:6]=1)=[NH:4])(=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 178513262HCID 178513262, compound

Product 1

HCID 178476700HCID 178476700, compoundYield 89%

Procedure

To a solution of 6 (262 mg, 0.8 mmol) in glacial acetic acid (8 mL) was slowly added acetic anhydride (0.28 mL). After stirring overnight, TLC indicated complete acylation of the starting material. The reaction mixture was poured onto ice water, the precipitate was filtered, washed with water and dried to give 7 in 89% yield, mp 212-213° C. 1H NMR (DMSO-d6); δ 2.17 (s, 6H), 6.85 (br s, 4H), 6.98 (d, J=3.6 Hz, 1H), 7.00 (d, J=3.6 Hz, 1H), 7.14 (d, J=3.6Hz, 1H), 7.24 (d, J=3.6 Hz, 1H), 7.79 (d, J=8.4 Hz, 2H), 7.87 (d, J=8.4 Hz, 2H). 13C NMR (DMSO-d6); δ 168.4, 168.1, 155.8, 152.4, 148.9, 146.1, 144.8, 144.3, 131.2, 130.6, 127.2, 123.3, 113.1, 109.6, 109.3, 107.6, 19.8, 19.7. Calcd for C20H18N4O6: C, 58.53; H, 4.42. Found. C, 58.71; H, 4.50.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customto give 7 in 89% yield, mp 212-213° C

Sources & evidence

ORD record
ord-636c79c3c24f4baf9c30cc6ca43096eb
Source dataset
uspto-grants-2009_04
Patent number
US07517893B2

Reaction notes

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