Formic Acid → N-(2,4-dimethylphenyl)-4-(1-hydroxy-3-(2H-tetrazol-5-yl)propyl)-N-isobutylbenzenesulfonamide

HRID 1746435Notes

Reaction equation

HRID 1746435 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:47][CH:48]([CH3:50])[CH3:49])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:46])[CH2:20][CH2:21][C:22]2[N:23]=[N:24][N:25](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:26]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11].Cl.C(O)(C)C.C(O)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:47][CH:48]([CH3:50])[CH3:49])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH:19]([OH:46])[CH2:20][CH2:21][C:22]2[N:26]=[N:25][NH:24][N:23]=2)=[CH:17][CH:18]=1)(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 86731599N-(2,4-dimethylphenyl)-4-(1-hydroxy-3-(2-trityl-2H-tetrazol-5-yl)propyl)-N-isobutylbenzenesulfonamide

Product 1

HCID 71543471N-(2,4-dimethylphenyl)-4-(1-hydroxy-3-(2H-tetrazol-5-yl)propyl)-N-isobutylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

N-(2,4-dimethylphenyl)-4-(1-hydroxy-3-(2-trityl-2H-tetrazol-5-yl)propyl)-N-isobutylbenzenesulfonamide (20 mg, 0.029 mmol), at room temperature was treated with a solution of HCl (6N in isopropanol, 2 mL, 12.00 mmol) and isopropanol (2 mL). The reaction mixture was stirred at 20° C. for 2 hours, then the solvent evaporated in vacuo and the crude partitioned between ethyl acetate (5 mL) and water (5 mL). The organic phase was separated by hydrophilic frit then evaporated in vacuo to give a residue. LCMS analysis showed the reaction was incomplete, so the residue was re-dissolved in dichloromethane (DCM) (2 mL) and treated with formic acid (0.5 mL, 13.04 mmol). The solution was left to stand for 2 hours. The solvent was evaporated in vacuo then dissolved in a 1:1 mixture of MeOH and DMSO and purified by MDAP (Method F) to give the required product, 3.69 mg. LCMS (M+1) 444, RT 1.09 mins.

Workup

  1. customthe solvent evaporated in vacuo
  2. customthe crude partitioned between ethyl acetate (5 mL) and water (5 mL)
  3. customThe organic phase was separated by hydrophilic frit
  4. customthen evaporated in vacuo
  5. customto give a residue
  6. waitThe solution was left
  7. waitto stand for 2 hours
  8. customThe solvent was evaporated in vacuo
  9. dissolutionthen dissolved in a 1:1 mixture of MeOH and DMSO
  10. custompurified by MDAP (Method F)

Sources & evidence

ORD record
ord-ec8d0d30fb54431c87ba1c4c748f9012
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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