Trimethylsilylacetylene → HCID 178499341, compound

HRID 244907Notes

Reaction equation

HRID 244907 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:29]#[C:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[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].[CH3:35][Si:36]([C:39]#[CH:40])([CH3:38])[CH3:37]>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:29]#[C:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[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:40]=[C:39]([Si:36]([CH3:38])([CH3:37])[CH3:35])[N:28]=[N:27]2)[CH2:22][CH2:21]1)=[O:4]

Participants

3

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 178499342HCID 178499342, compound

Product 1

HCID 178499341HCID 178499341, compound

Procedure

A solution of 3-[(trans-4-azido-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (1.0 g, 2.0 mmol) in trimethylsilylacetylene (1.4 ml, 10 mmol) is treated in microwave at 120° C. for 2 h. The mixture is concentrated under reduced pressure and the residue is purified by silica gel column chromatography (5% ethyl acetate/hexane to 100% ethyl acetate) to afford 5-(3,3-dimethyl-but-1-ynyl)-3-{(trans-4-methyl-cyclohexanecarbonyl)-[trans-4-(4-trimethylsilanyl-[1,2,3]triazol-1-yl)-cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customthe residue is purified by silica gel column chromatography (5% ethyl acetate/hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-216610f3606147908000796e3a74504c
Source dataset
uspto-grants-2014_02
Patent number
US08658674B2

Reaction notes

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