Hydrochloric Acid → HCID 22220078, compound

HRID 1794101Notes

Reaction equation

HRID 1794101 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[S:33])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:34]>C(OCC)(=O)C>[ClH:34].[N:11]1([C:14](=[S:33])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][S:24]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)(=[O:26])=[O:25])=[CH:19][CH:18]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22219902HCID 22219902, compound

Product 1

HCID 22220078HCID 22220078, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

to a stirred solution of 4-benzenesulfonyloxybenzyl 4-tert-butoxycarbonylpiperazine-1-thiocarboxylate (44 mg) in ethyl acetate (2 mL) was added hydrogen chloride solution (4M, dioxane, 0.23 mL). The mixture was stirred for 18 h then concentrated under vacuum to give the product as a white crystalline solid (31 mg, 78%): HPLC (XTERRA, 50/80, 220 nm) 98.4% (2.54 min); NMR δH (400 MHz, DMSO-d6) 3.100(4H, bt), 3.672(4H, bt), 4.123(2H, s), 6.976(2H, d, J 8.5 Hz), 7.341(2H, d, J 9.0 Hz), 7.680(2H, t, J 8.0 Hz), 7.826(1H, t, J 7.5 Hz), 7.870(2H, d, J 7.0 Hz) and 9.258(2H, bs).

Workup

  1. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-4dc4beec5acb4874a6a1d0114a4175cd
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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