Ethanol → Tert-butyl 4-(2-ethoxy-1-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)-2-oxoethyl)piperidine-1-carboxylate

HRID 335152Notes

Reaction equation

HRID 335152 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[N:13]=[CH:12][C:11]([S:14][CH2:15][CH2:16]C(OC)=O)=[CH:10][C:9]=2[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:5][CH:6]=1.ClC(Cl)(Cl)C([CH:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1)O.[CH2:47]([O-:49])[CH3:48].[Na+].C([OH:53])C>>[CH2:47]([O:49][C:16](=[O:53])[CH:15]([CH:32]1[CH2:33][CH2:34][N:35]([C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH2:36][CH2:37]1)[S:14][C:11]1[CH:12]=[N:13][C:8]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)=[C:9]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]=1)[CH3:48]

Participants

5

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 24765636Methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoateHCID 66995190Tert-butyl 4-(2,2,2-trichloro-1-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 86631501Tert-butyl 4-(2-ethoxy-1-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)-2-oxoethyl)piperidine-1-carboxylateYield 75.5%

Procedure

Placed methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate (2.20 g, 5.48 mmol), tert-butyl 4-(2,2,2-trichloro-1-hydroxyethyl)piperidine-1-carboxylate (1.86 g, 5.59 mmol), and sodium ethanolate (3.55 g, 10.9 mmol) in ethanol (75 mL) and stirred at ambient temperature for 4 hours. The reaction was quenched with sat NH4Cl and extracted with CH2Cl2. The organic phase was concentrated and purified by silica gel (10-25% EtOAc in hex) to give the title compound (2.63 g, 75.5% yield).

Workup

  1. customThe reaction was quenched with sat NH4Cl
  2. extractionextracted with CH2Cl2
  3. concentrationThe organic phase was concentrated
  4. custompurified by silica gel (10-25% EtOAc in hex)

Sources & evidence

ORD record
ord-df1b6ab6d8f0459fbd2e6b474c3ea034
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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