Pyridine → HCID 178499291, compound

HRID 1190051Notes

Reaction equation

HRID 1190051 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:42]2[CH2:47][CH2:46][C:45]([CH3:49])([CH3:48])[CH2:44][CH2:43]2)=[CH:8][C:9]=1[N:10]([CH:20]([CH2:33][O:34][SiH](C(C)C)C(C)C)[CH2:21][O:22][Si](C(C)C)(C(C)C)C(C)C)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:42]2[CH2:43][CH2:44][C:45]([CH3:48])([CH3:49])[CH2:46][CH2:47]2)=[CH:8][C:9]=1[N:10]([CH:20]([CH2:33][OH:34])[CH2:21][OH:22])[C:11]([C@H:13]1[CH2:14][CH2:15][C@H:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12])=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 178499292HCID 178499292, compound

Product 1

HCID 178499291HCID 178499291, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[(1-diisopropylsilanyloxymethyl-2-triisopropylsilanyloxy-ethyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(4,4-dimethyl-cyclohexyl)-thiophene-2-carboxylic acid methyl ester (60 mg, 0.078 mmol) in THF (1 mL) was treated with HF.pyridine (0.1 mL). The mixture was stirred at room temperature for 16 h. The mixture was diluted with EtOAc and added to solid NaHCO3. It was stirred at room temperature for 2 h, filtered and evaporated. Pure 5-(4,4-dimethyl-cyclohexyl)-3-[(2-hydroxy-1-hydroxymethyl-ethyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester was obtained on chromatography over silica gel (EtOAc as eluent) (32 mg, 89%).

Workup

  1. stirringIt was stirred at room temperature for 2 h
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-df178d7f91c64465b8c54705ca8f99a8
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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