Acetyl chloride → HCID 68862592, compound

HRID 2109413Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][C:34]=1[OH:35])[C:9]([NH:11][NH:12][C:13]([C:15]1[O:16][CH:17]=[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:14])=[O:10].C(N(C(C)C)C(C)C)C>O1CCOCC1>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][C:34]=1[OH:35])[C:9]([NH:11][NH:12][C:13]([C:15]1[O:16][CH:17]=[C:18]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:14])=[O:10])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

Acetyl chloride (0.17 ml) was added to a mixture of the compound of Example 42 (0.83 g), ethyldiisopropylamine (1.05 ml) and dioxane (10 ml) at 0° C., allowed to be warmed to 25° C. and stirred for 9 days. The solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate and washed with 1 M hydrochloric acid and saturated brine. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) and recrystallized from ethyl acetate/hexane, thereby giving 0.25 g of the desired compound. Melting point: 233-235° C.

Workup

customThe solvent was evaporated under reduced pressure
additionThe residue was diluted with ethyl acetate
washwashed with 1 M hydrochloric acid and saturated brine
dry with materialThe organic layer was dried over MgSO4
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: chloroform)
customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-cb569979601b464c9b3da2caef1fb051
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514452B2

Reaction notes

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