Dichloromethane → Methanesulfonic acid 2-butyl-5-chloro-3-[2'-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-ylmethyl ester

HRID 1746867Notes

Reaction equation

HRID 1746867 reaction equation
C(Cl)Cl.[CH2:4]([C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30]([C:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:11]([CH2:50][OH:51])=[C:10]([Cl:52])[N:9]=1)[CH2:5][CH2:6][CH3:7].[CH3:53][S:54](Cl)(=[O:56])=[O:55].C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH2:4]([C:8]1[N:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30]([C:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]=[N:28][N:27]=3)=[CH:18][CH:19]=2)[C:11]([CH2:50][O:51][S:54]([CH3:53])(=[O:56])=[O:55])=[C:10]([Cl:52])[N:9]=1)[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 11643218(2-Butyl-4-chloro-1-((2'-(1-trityl-1H-tetraazol-5-YL)(1,1'-biphenyl)-4-YL)methyl)-1H-imidazol-5-YL)methanol

Product 1

HCID 86624363Methanesulfonic acid 2-butyl-5-chloro-3-[2'-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-ylmethyl esterYield 98.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a DCM (200 mL) solution of intermediate (11b) (13.6 g, 20.4 mmol), cooled to −78° C., was added methane sulfonyl chloride (6.3 mL, 81.6 mmol). The mixture was stirred at −78° C. for 15 minutes. A saturated NaHCO3 solution (100 mL) and EtOAc (500 mL) were added to the cooled mixture, which was then allowed to reach room temperature. The organic was washed an additional three times with saturated aqueous NaCl (100 mL). After drying over sodium sulfate and filtration, the removal of solvent provided intermediate (11c) as a yellow oil (15 g) which was used directly in the next step. MS m/z: [M+H+] calcd for C42H39ClN6O3S, 743.26; due to the reactive nature of intermediate (11c), only the methanol substituted product was observed upon running a mass spectrum of the sample when dissolved in methanol; methanol substituted product [M+H+]=679.6.

Workup

  1. customto reach room temperature
  2. washThe organic was washed an additional three times with saturated aqueous NaCl (100 mL)
  3. dry with materialAfter drying over sodium sulfate and filtration
  4. customthe removal of solvent

Sources & evidence

ORD record
ord-72c59eaff4034c6d84a14a8bec8d8786
Source dataset
uspto-grants-2015_10
Patent number
US09150514B2

Reaction notes

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