Chlorotrimethylsilane → HCID 66849422, compound

HRID 1046451Notes

Reaction equation

HRID 1046451 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[CH3:6][O:7][C:8]([C:10]1[S:11][C:12]([C:39]#[C:40][C:41]([CH3:46])([CH3:45])[CH2:42][CH2:43][OH:44])=[CH:13][C:14]=1[N:15]([CH:25]1[CH2:30][CH2:29][CH:28]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:27][CH2:26]1)[C:16]([CH:18]1[CH2:23][CH2:22][CH:21]([CH3:24])[CH2:20][CH2:19]1)=[O:17])=[O:9].C(N(CC)CC)C>ClCCl>[CH3:6][O:7][C:8]([C:10]1[S:11][C:12]([C:39]#[C:40][C:41]([CH3:45])([CH3:46])[CH2:42][CH2:43][O:44][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:13][C:14]=1[N:15]([CH:25]1[CH2:30][CH2:29][CH:28]([O:31][Si:32]([C:35]([CH3:36])([CH3:37])[CH3:38])([CH3:34])[CH3:33])[CH2:27][CH2:26]1)[C:16]([CH:18]1[CH2:19][CH2:20][CH:21]([CH3:24])[CH2:22][CH2:23]1)=[O:17])=[O:9]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 58114127HCID 58114127, compound

Product 1

HCID 66849422HCID 66849422, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TMSCl (0.08 mL, 0.596 mmol) was added dropwise to a solution of 3-[[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-(4-methyl-cyclohexanecarbonyl)-amino]-5-(5-hydroxy-3,3-dimethyl-pent-1-ynyl)-thiophene-2-carboxylic acid methyl ester (300 mg, 0.497 mmol) and triethylamine (0.11 mL, 0.745 mmol) in dichloromethane at 0° C. After stirring for 1 h, the reaction was warmed to room temperature and stirred for an additional 1.5 h. The solution was washed with water, brine, dried and concentrated to give crude 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 (330 mg) which was carried to next step without further purification.

Workup

  1. stirringstirred for an additional 1.5 h
  2. washThe solution was washed with water, brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0c7afc5ba13843d7b90484004e278e20
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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