Calcium Hydroxide → HCID 70978124, compound

HRID 2281061Notes

Reaction equation

HRID 2281061 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:16]4[CH:30]=[CH:29][C:19]([CH2:20][N:21]5[CH2:25][C:24](=[O:26])[N:23]([CH3:27])[C:22]5=[O:28])=[C:18]([F:31])[CH:17]=4)=[C:13]([S:14][CH3:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.[OH-:32].[Ca+2].[OH-:34]>C(Cl)(Cl)Cl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:16]4[CH:30]=[CH:29][C:19]([CH2:20][N:21]5[CH2:25][C:24](=[O:26])[N:23]([CH3:27])[C:22]5=[O:28])=[C:18]([F:31])[CH:17]=4)=[C:13]([S:14]([CH3:15])(=[O:34])=[O:32])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6093208Calcium HydroxideHCID 70978427HCID 70978427, compound

Product 1

HCID 70978124HCID 70978124, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-{4-[1-(cyclopropylmethyl)-4-(methylsulfanyl)-1H-benzotriazol-5-yl]-2-fluorobenzyl}-3-methylimidazolidine-2,4-dione (Example 15, 14 mg, 0.032 mmol) in chloroform (0.45 mL) at 0° C. was added meta-peroxychlorobenzoic acid (7.1 mg, 0.032 mmol). The mixture was stirred for 1.5 hours at 0° C. and then warmed to ambient temperature and stirred for an additional 14 hours. The mixture was cooled to 0° C. and treated with calcium hydroxide (3.3 mg, 0.045 mmol), stirred for 30 minutes and filtered. The filtrate was concentrated in vacuo and purified via preparative reversed-phase HPLC (5-95% MeCN/water+0.1% TFA) to provide the title compound: 1H NMR (400 MHz, CDCl3) 7.82 (d, 1H, J=8.0 Hz), 7.42 (d, 1H, J=8.8 Hz), 7.39 (t, 1H, J=7.6 Hz), 7.17-7.23 (m, 2H), 4.70 (s, 2H), 4.61 (d, 2H, J=7.2 Hz), 3.89 (s, 2H), 3.67 (s, 3H), 3.06 (s, 3H), 1.41-1.47 (m, 1H), 0.71-0.76 (m, 2H), 0.54-0.58 (m, 2H) ppm. LRMS m/z (M+H) 472.2 found, 472.1 required.

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for an additional 14 hours
  3. temperatureThe mixture was cooled to 0° C.
  4. stirringstirred for 30 minutes
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. custompurified via preparative reversed-phase HPLC (5-95% MeCN/water+0.1% TFA)

Sources & evidence

ORD record
ord-04adbc571ce94d52beed078ca46a8db2
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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