Water → (+/-)-5-(2-Methyl-propane-2-sulfinylamino)-2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-pentanoic acid methyl ester

HRID 858910Notes

Reaction equation

HRID 858910 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:9]1[N:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[N:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[CH2:5][CH2:6][CH:7]=O.[CH3:27][C:28]([S:31]([NH2:33])=[O:32])([CH3:30])[CH3:29].O.[BH4-].[Na+]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:9]1[N:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[N:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[CH2:5][CH2:6][CH2:7][NH:33][S:31]([C:28]([CH3:30])([CH3:29])[CH3:27])=[O:32]

Participants

7

Reactant 4

HCID 962Water2×HCID 3382465Tert-ButanesulfinamideHCID 4311764Sodium borohydrideHCID 587635832-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-5-oxo-pentanoic acid methyl ester

Product 1

HCID 58763604(+/-)-5-(2-Methyl-propane-2-sulfinylamino)-2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-pentanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a magnetically stirred solution of 2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-5-oxo-pentanoic acid methyl ester 44a (0.066 g, 0.189 mmol) in THF (2 mL) at room temperature under Ar atmosphere was added 2-methyl-propane-2-sulfinic acid amide (0.023 g, 0.189 mmol) and titanium ethoxide (20 wt % solution in ethanol, 2 mL). The reaction mixture was stirred overnight at room temperature. Water (40 mL) was added, and the aqueous phase was extracted with ethyl acetate (2×40 mL). The combined organic layers were washed with water, dried (MgSO4), and concentrated in vacuo. The reaction mixture was redisolved in MeOH (2 mL) and sodium borohydride (0.014 mg, 0.378 mmol) was added at room temperature. The reaction mixture was stirred for 1 h at room temperature, then water (40 mL) was added, and the aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water, dried (MgSO4), and concentrated in vacuo to provide crude product.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×40 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. stirringThe reaction mixture was stirred for 1 h at room temperature
  6. extractionthe aqueous phase was extracted with ethyl acetate (2×100 mL)
  7. washThe combined organic layers were washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customto provide crude product

Sources & evidence

ORD record
ord-0045dff9b0664f90b7b34ce6186aa434
Source dataset
uspto-grants-2006_12
Patent number
US07148353B2

Reaction notes

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