Hydrochloric Acid → HCID 59420747, compound

HRID 1253821Notes

Reaction equation

HRID 1253821 reaction equation
[F:1][C:2]([F:26])([F:25])[CH2:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:13][Si](C(C)C)(C(C)C)C(C)C)[CH:10]=2)[C:5]1=[O:24].Cl>CO.O1CCCC1>[SH:13][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5](=[O:24])[N:4]([CH2:3][C:2]([F:25])([F:1])[F:26])[CH2:12]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59420727HCID 59420727, compound

Product 1

HCID 59420747HCID 59420747, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(2,2,2-trifluoroethyl)-5-(triisopropylsilylthio)-isoindolin-1-one (1.39 g, 3.45 mmol) was dissolved in a solution of hydrochloric acid (6.7 ml, 1.25 M, 8.62 mmol) in methanol (10 ml) and tetrahydrofuran (10 ml) and stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo to afford the desired compound as an off-white solid (0.783 g, 92% yield). 1H NMR (CDCl3, 400 MHz) 3.70 (1H, s), 4.22 (2H, q), 4.53 (2H, s), 7.35-7.39 (2H, m) and 7.76 (1H, d); MS (ES+) 248, (ES−) 246.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e02b011fbffd46b7861ac70c305f3961
Source dataset
uspto-grants-2013_06
Patent number
US08455507B2

Reaction notes

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