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Trifluoroacetic acid → Trifluoroacetic acid

HRID 853674
Notes
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Reaction equation

HRID 853674 reaction equation
C([O:14][C:15]1[C:16]2[C:44](=[O:45])[N:43]([CH2:46][C:47]3[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=3)[CH2:42][C:17]=2[C:18]([O:25][S:26]([CH2:29][CH2:30][N:31]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]2=[O:41])(=[O:28])=[O:27])=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)(C1C=CC=CC=1)C1C=CC=CC=1.[F:54][C:55]([F:60])([F:59])[C:56]([OH:58])=[O:57].C([SiH](CC)CC)C>ClCCl>[F:53][C:50]1[CH:49]=[CH:48][C:47]([CH2:46][N:43]2[C:44](=[O:45])[C:16]3[C:15]([OH:14])=[C:24]4[C:19]([CH:20]=[CH:21][CH:22]=[N:23]4)=[C:18]([O:25][S:26]([CH2:29][CH2:30][N:31]4[C:39](=[O:40])[C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[C:32]4=[O:41])(=[O:28])=[O:27])[C:17]=3[CH2:42]2)=[CH:52][CH:51]=1.[C:56]([OH:58])([C:55]([F:60])([F:59])[F:54])=[O:57]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 589289312-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester

Product 2

HCID 6422Trifluoroacetic acidYield 76%
HCID 10099364
2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid 7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 268 (12.2 mg, 0.017 mmol) dissolved in dichloromethane (1 mL) was added trifluoroacetic acid (100 μl) and triethylsilane (200 μl). The reaction mixture was stirred at room temperature for ½ hours under an inert atmosphere then concentrated in vacuo. The residue was triturated with diethyl ether/hexane (1/1) to afford 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid 7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester 269, TFA salt, (9.0 mg, 76%) as a yellow solid: 1H NMR (CDCl3) δ 9.0 (d, 1H), 8.5 (dd, 1H), 7.9 (m, 2H), 7.8 (m, 2H), 7.7 (m, 1H), 7.3 (m, 2H), 7.0 (t, 2H), 4.8 (s, 2H), 4.6 (s, 2H), 4.4 (q, 2H), 3.9 (q, 2H); MS: 562 (M+1).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was triturated with diethyl ether/hexane (1/1)

Sources & evidence

ORD record
ord-ca5895e5b22e40789051a051cdd9635f
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253180B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes