Sodium Azide → HCID 178499295, compound

HRID 1190032Notes

Reaction equation

HRID 1190032 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:31]2[CH2:36][CH2:35][C:34]([CH3:38])([CH3:37])[CH2:33][CH2:32]2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@@H:23](OS(C)(=O)=O)[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].[N-:39]=[N+:40]=[N-:41].[Na+]>CN(C=O)C.C(OCC)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:31]2[CH2:36][CH2:35][C:34]([CH3:38])([CH3:37])[CH2:33][CH2:32]2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([N:39]=[N+:40]=[N-:41])[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]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 178499301HCID 178499301, compound

Product 1

HCID 178499295HCID 178499295, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-(4,4-dimethyl-cyclohexyl)-3-[(cis-4-methanesulfonyloxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (2.56 g, 4.50 mmol) in 30 ml of DMF was added sodium azide (1.5 g, 23 mmol). The reaction mixture was stirred for 48 h at 50° C. The mixture was diluted with diethyl ether and washed 3 time with water and 1 time with brine. The organic layer was dried with sodium sulfate, filtered and concentrated under reduce pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane to 100% ethyl acetate followed by 10% MeOH/CH2Cl2) to give 3-[(trans-4-Azido-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(4,4-dimethyl-cyclohexyl)-thiophene-2-carboxylic acid methyl ester (1.6 g, 69%).

Workup

  1. washwashed 3 time with water and 1 time with brine
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane to 100% ethyl acetate followed by 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6ee7acffc6dd4e2aa53256be0684f0f0
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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