Acetic Anhydride → 9-(4-(1-(tert-Butoxycarbonylamino)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl acetate

HRID 1853832Notes

Reaction equation

C(O[C:5]([O:7][C:8]1[CH:17]=[CH:16][C:15]2[NH:14][C:13](=[O:18])[C:12]3[S:19][CH:20]=[CH:21][C:11]=3[C:10]=2[C:9]=1[C:22]1[CH:27]=[CH:26][C:25]([CH:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH3:29])=[CH:24][CH:23]=1)=[O:6])(C)C.[C:38](OC(=O)C)(=O)C>>[C:5]([O:7][C:8]1[CH:17]=[CH:16][C:15]2[NH:14][C:13](=[O:18])[C:12]3[S:19][CH:20]=[CH:21][C:11]=3[C:10]=2[C:9]=1[C:22]1[CH:27]=[CH:26][C:25]([CH:28]([NH:30][C:31]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:37])[CH3:29])=[CH:24][CH:23]=1)(=[O:6])[CH3:38]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 67457829Tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Product 1

HCID 674503849-(4-(1-(tert-Butoxycarbonylamino)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl acetateYield 63%

Procedure

Following Procedure Preparing tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate, (44 mg, 0.10 mmol) was reacted with acetic anhydride (11 μL, 0.12 mmol) to afford the desired product (30 mg, 63%) as a solid: ESI MS m/z 479 [C26H26N2O5S+H]+.

Sources & evidence

ORD record: ord-56585a1f757141f3a784631435f9586f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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