Hydrochloric Acid → HCID 72189290, compound

HRID 1487086Notes

Reaction equation

HRID 1487086 reaction equation
[Li+].[B-](CC)(CC)CC.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:40][CH:41]([CH3:43])[CH3:42])[S:18]([C:21]2[CH:22]=[CH:23][C:24]([C:31](=[O:39])[CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[C:25]([CH:30]=2)[C:26](OC)=[O:27])(=[O:20])=[O:19])=[CH:13][CH:12]=1)[CH3:10].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:40][CH:41]([CH3:42])[CH3:43])[S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH:31]([OH:39])[CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[C:25]([CH2:26][OH:27])[CH:30]=2)(=[O:19])=[O:20])=[CH:13][CH:12]=1)[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23712863Lithium triethylborohydrideHCID 89876426HCID 89876426, compound

Product 1

HCID 72189290HCID 72189290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Super-Hydride® (1 M in tetrahydrofuran, 0.388 mL, 0.388 mmol) was added slowly to a solution of methyl 5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)-2-(2-morpholinoacetyl)benzoate (65 mg, 0.129 mmol) in tetrahydrofuran (THF) (0.5 mL) at room temperature, under nitrogen. The solution was stirred for 16 hours, then treated with HCl (2 N, 2 mL) and stirred for 10 minutes. The mixture was basified with sodium bicarbonate solution and extracted with ethyl acetate (2×5 mL). The organics were dried (MgSO4) then evaporated and purification of the crude attempted on a silica (Si) cartridge eluting with 5% methanol-dichloromethane+0.5% ammonia, although this gave poor separation. Purification was successfully achieved using a silica (Si) cartridge eluting with 1-3% methanol-dichloromethane+0.1-0.3% ammonia to give the desired product as a cream solid, 31 mg. LCMS [LCMS1] Rt 0.90 min, m/z (ES+) 477 (M+H).

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted with ethyl acetate (2×5 mL)
  3. dry with materialThe organics were dried (MgSO4)
  4. customthen evaporated
  5. custompurification of the crude
  6. washeluting with 5% methanol-dichloromethane+0.5% ammonia, although this gave poor separation
  7. customPurification
  8. washeluting with 1-3% methanol-dichloromethane+0.1-0.3% ammonia

Sources & evidence

ORD record
ord-1a29875ca3704c3b9e7eeca50b95b5ac
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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