Trimethylsilylacetylene → HCID 178499294, compound

HRID 2099653Notes

Reaction equation

HRID 2099653 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:29]2[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[CH2:31][CH2:30]2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([N:26]=[N+:27]=[N-:28])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:29]2[CH2:30][CH2:31][C:32]([CH3:35])([CH3:36])[CH2:33][CH2:34]2)=[CH:8][C:9]=1[N:10]([C:11]([C@H:13]1[CH2:14][CH2:15][C@H:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12])[C@H:20]1[CH2:25][CH2:24][C@H:23]([N:26]2[CH:42]=[C:41]([Si:38]([CH3:40])([CH3:39])[CH3:37])[N:28]=[N:27]2)[CH2:22][CH2:21]1)=[O:4]

Participants

3

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 178499295HCID 178499295, compound

Product 1

HCID 178499294HCID 178499294, compoundYield 105.6%

Procedure

A solution of 3-[(trans-4-azido-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(4,4-dimethyl-cyclohexyl)-thiophene-2-carboxylic acid methyl ester (0.90 g, 1.7 mmol) in trimethylsilylacetylene (1.2 ml, 6.8 mmol) was treated in microwave at 120° C. for 2 h. The mixture was concentrated under reduce pressure and the residue purified by silica gel column chromatography (1% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2) to obtain 5-(4,4-Dimethyl-cyclohexyl)-3-{(trans-4-methyl-cyclohexanecarbonyl)-[trans-4-(4-trimethylsilany-[1,2,3]triazol-1-yl)-cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester (1.1 g, 58%)

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by silica gel column chromatography (1% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-03eb0e29877a47229fa36108cb71b19c
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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