Triethylsilane → HCID 58113857, compound

HRID 1046452Notes

Reaction equation

HRID 1046452 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:34]#[C:35][C:36]([CH3:45])([CH3:44])[CH2:37][CH2:38][O:39][Si](C)(C)C)=[CH:8][C:9]=1[N:10]([CH:20]1[CH2:25][CH2:24][CH:23]([O:26][Si](C(C)(C)C)(C)C)[CH2:22][CH2:21]1)[C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].[O:46]1[CH2:51][CH2:50][C:49](=O)[CH2:48][CH2:47]1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>[N+](C)([O-])=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:34]#[C:35][C:36]([CH3:45])([CH3:44])[CH2:37][CH2:38][O:39][CH:49]2[CH2:50][CH2:51][O:46][CH2:47][CH2:48]2)=[CH:8][C:9]=1[N:10]([CH:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1)[C:11]([CH:13]1[CH2:14][CH2:15][CH:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12])=[O:4]

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 66849422HCID 66849422, compound

Product 1

HCID 58113857HCID 58113857, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

3-[[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-(4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-5-trimethylsilanyloxy-pent-1-ynyl)-thiophene-2-carboxylic acid methyl ester (230 mg, 0.34 mmol) was added to a solution of tetrahydro-pyran-4-one (29 mg, 0.29 mmol) and FeCl3 (2.8 mg, 0.017 mmol) in nitromethane (5.0 mL) at 0° C. Triethylsilane (0.054 mL, 0.34 mmol) was added and the reaction warmed to room temperature and stirred for 2 h. Sat. NaHCO3 was added and the reaction extracted with dichloromethane. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to give the crude product. Purification by HPLC with CH3CN (0.1% TFA)/H2O (0.1% TFA) provided 5-[3,3-dimethyl-5-(tetrahydro-pyran-4-yloxy)-pent-1-ynyl]-3-[(4-hydroxy-cyclohexyl)-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (8 mg, 4%) as solid.

Workup

  1. extractionthe reaction extracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification by HPLC with CH3CN (0.1% TFA)/H2O (0.1% TFA)

Sources & evidence

ORD record
ord-31d2f618889044f8ab8b3d353125ccf7
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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