Water → HCID 18957142, compound

HRID 2379475Notes

Reaction equation

HRID 2379475 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:42])[N:15]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:16]1[N:17]=[N:18][N:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29]C2CCCCO2)[N:20]=1)[CH3:3].O.O.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:3][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:11])[CH3:12])[C:5]=1[NH:13][C:14](=[O:42])[N:15]([C:16]1[N:17]=[N:18][N:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[N:20]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 15230642HCID 15230642, compound

Product 1

HCID 18957142HCID 18957142, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred, room temperature solution of (±)N'-[2,6-bis(1-methylethyl)phenyl-N-phenyl-N-[2-[8-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-tetrazol-5-yl]-urea (2.1600 g, 0.0037449 mol) in methanol (20 mL) was added dropwise water (1.0 mL) and 4-methylbenzenesulfonic acid monohydrate (0.0594 g, 0.000312 mol), and the mixture was stirred. After 46 hours the mixture was rotoevaporated, and the residue was chromatographed on silica gel (230 g, 230-400 mesh) using PET ether-diethyl ether (1:2, 15×200 mL) as eluent. Fractions containing product were rotoevaporated from dichloromethane to an oil. The oil was dried in vacuo (95° C., 15 min; 17h, 25° C.) to give the title compound, yield 1.482 g (80%). 1H NMR (CDCl3): δ 9.2 (br s, 1H), 7.5 (t, 2H), 7.4 (m, 3H), 7.3 (d, 1H), 7.2 (d, 2H), 4.5 (t, 2H), 3.6 (t, 2H), 3.2 (septet, 2H), 2.0 (m, 2H), 1.5 (m, 4H), 1.3 (m, 6H), 1.2 (d, 12H).

Workup

  1. customthe residue was chromatographed on silica gel (230 g, 230-400 mesh)
  2. additionFractions containing product
  3. dry with materialThe oil was dried in vacuo (95° C., 15 min; 17h, 25° C.)

Sources & evidence

ORD record
ord-55fd43bc1e3e45f3a7c9d5666afcaffc
Source dataset
uspto-grants-1994_11
Patent number
US05362744

Reaction notes

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