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Trifluoroacetic acid → N-Cyclopropyl-3-fluoro-5-[2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-4-{[(8aR)-3-oxotetrahydro[1,3]oxazolo[3,4-a]pyrazin-7(1H)-yl]sulfonyl}-1,2-dihydroisoquinolin-6-yl]-4-methylbenzamide

HRID 906452
Notes
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Reaction equation

HRID 906452 reaction equation
[Si]([O:8][CH2:9][C:10]([CH3:56])([CH3:55])[CH2:11][N:12]1[CH:21]=[C:20]([S:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33]C(C)(C)C)=[O:32])[C@@H:27]([CH2:38]O)[CH2:26]2)(=[O:24])=[O:23])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:40]3[CH:45]=[C:44]([C:46](=[O:51])[NH:47][CH:48]4[CH2:50][CH2:49]4)[CH:43]=[C:42]([F:52])[C:41]=3[CH3:53])[CH:18]=2)[C:13]1=[O:54])(C(C)(C)C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[CH:48]1([NH:47][C:46](=[O:51])[C:44]2[CH:45]=[C:40]([C:17]3[CH:18]=[C:19]4[C:14](=[CH:15][CH:16]=3)[C:13](=[O:54])[N:12]([CH2:11][C:10]([CH3:56])([CH3:55])[CH2:9][OH:8])[CH:21]=[C:20]4[S:22]([N:25]3[CH2:30][CH2:29][N:28]4[C:31](=[O:32])[O:33][CH2:38][C@H:27]4[CH2:26]3)(=[O:24])=[O:23])[C:41]([CH3:53])=[C:42]([F:52])[CH:43]=2)[CH2:49][CH2:50]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86640972tert-Butyl (2R)-4-({2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxo-1,2-dihydroisoquinolin-4-yl}sulfonyl)-2-(hydroxymethyl)piperazine-1-carboxylate

Product 1

HCID 67389817N-Cyclopropyl-3-fluoro-5-[2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-4-{[(8aR)-3-oxotetrahydro[1,3]oxazolo[3,4-a]pyrazin-7(1H)-yl]sulfonyl}-1,2-dihydroisoquinolin-6-yl]-4-methylbenzamide

Reagents, catalysts & solvents

2
HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2R)-4-({2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxo-1,2-dihydroisoquinolin-4-yl}sulfonyl)-2-(hydroxymethyl)piperazine-1-carboxylate (Example 49c, 0.537 g) was dissolved in DCM (10 mL) and treated with trifluoroacetic acid (3 mL). The reaction mixture was diluted with toluene (5 mL) and evaporated under reduced pressure.

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f69bb622365f4cac85999e9dff74149d
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08012980B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes