Acetic Anhydride → HCID 18976218, compound

HRID 2393599Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])C.C([O-])=O.[Na+].[O:12]=[C:13]1[C:21]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])([NH:22][C:23]([CH:25]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][NH:26]2)=[O:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]1[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)=O>[CH:1]([N:26]1[CH:25]([C:23]([NH:22][C:21]2([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:13]2=[O:12])=[O:24])[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27]1)=[O:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 0.66 g of formic acid and 1.35 g of acetic acid anhydride was heated at 50° C. for 15 minutes. After cooling by dilution with 15 ml of anhydrous methylene chloride, 0.68 g of sodium formate and 15 ml of a methylene chloride solution of 1.70 g of ethyl 3-[2,3-dihydro-2-oxo-1-pentyl-3-(1,2,3,4-tetrahydro-3-isoquinolinyl)carbonylamino-1H-indol-3-yl]propionate were added to this mixed anhydride solution. The whole was stirred at room temperature overnight. The reaction mixture was neutralized with an aqueous saturated sodium hydrogen carbonate solution and then extracted with chloroform. The extract was washed, dried, filtered and then evaporated in vacuo to afford 1.72 g of ethyl 3-[3-(2-formyl-1,2,3,4-tetrahydro-3-isoquinolinyl)carbonylamino-2,3-dihydro-2-oxo-1-pentyl-1H-indol-3- yl]propionate as a pale yellow amorphous solid. IR (Nujol) (cm-1): 3280, 1720, 1655, 1610, FAB-MS (m/z): 506 (MH+) 160 (base).

Workup

extractionextracted with chloroform
washThe extract was washed
customdried
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-f781cdbacede427abac9e013bb116a1a
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807883

Reaction notes

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