Hydrochloric Acid → HCID 54410732, compound

HRID 482106Notes

Reaction equation

HRID 482106 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([O:29][S:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])(=[O:32])=[O:31])[CH:19]=[CH:20][C:21]=2[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([O:29][S:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])(=[O:31])=[O:32])[CH:19]=[CH:20][C:21]=2[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53650549HCID 53650549, compound

Product 1

HCID 54410732HCID 54410732, compoundYield 121.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 380 mg (0.666 mmol) of 2-chlorobenzenesulfonic acid 3-[[1-N-(tert-butoxycarbonyl)piperidin-4-yl]methoxy]-4-benzylphenyl ester, as prepared in the preceding step, in 5 mL of methylene chloride was added 3 mL of 4N HCl in dioxane. The reaction mixture was stirred at ambient temperature for 1 h, carefully quenched with with saturated NaHCO3, dried (K2CO3), and concentrated to give 381 mg of crude title compound as an oil which was used as is in the next step. 1H-NMR (300 MHz, CDCl3) δ 7.96 (d, 1H), 7.54-7.63 (m, 2H), 7.34-7.40 (m, 1H), 7.08-7.24 (m, 4H), 6.91 (d, 1H, J=8 Hz), 6.66 (d, 1H, J=2 Hz), 6.54 (dd, 1H, J=2, 8 Hz), 3.88 (s, 2H), 3.66 (d, 2H, J=5 Hz), 3.10 (d, 2H, J=12 Hz), 2.62 (t, 2H, J=10 Hz), 1.1-1.2 (m, 4H). Mass spectrum (MALDI-TOF; gentisic acid matrix) calcd. for C25H26ClNO4 S: 472.1 (M+H). Found: 472.6.

Workup

  1. customcarefully quenched with with saturated NaHCO3
  2. dry with materialdried (K2CO3)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fbbc67d5761e4088a9d4a26393b7c43e
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

Loading…