Acetonitrile → Tert-butyl 2-(4-(4-(4-chlorophenethylcarbamoyl)phenoxy)-3-cyanophenyl)-2-diazoacetate

HRID 453561Notes

Reaction equation

HRID 453561 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:33]=[CH:32][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]CCCC)=[O:24])=[CH:18][C:17]=3[C:30]#[N:31])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.CC1C=CC(S([N:46]=[N+:47]=[N-])(=O)=O)=CC=1.[CH2:49]1[CH2:59][CH2:58]N2C(=NCCC2)CC1.[C:60](#N)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22](=[N+:46]=[N-:47])[C:23]([O:25][C:59]([CH3:49])([CH3:60])[CH3:58])=[O:24])=[CH:18][C:17]=3[C:30]#[N:31])=[CH:32][CH:33]=2)=[O:10])=[CH:34][CH:35]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 13661p-Toluenesulfonyl azideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86669063Butyl 2-(4-(4-(4-chlorophenethylcarbamoyl)phenoxy)-3-cyanophenyl)acetate

Product 1

HCID 86643292Tert-butyl 2-(4-(4-(4-chlorophenethylcarbamoyl)phenoxy)-3-cyanophenyl)-2-diazoacetate

Procedure

tent-Butyl 2-(4-(4-(4-chlorophenethylcarbamoyl)phenoxy)-3-cyanophenyl)acetate (0.400 g) and 4-methylbenzenesulfonyl azide (0.193 g) were dissolved in 5 ml of acetonitrile and treated with DBU (0.152 ml). The reaction was stirred for 4 hours, then concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried, filtered, concentrated onto silica gel and purified by silica gel chromatography to provide tert-butyl 2-(4-(4-(4-chlorophenethylcarbamoyl)phenoxy)-3-cyanophenyl)-2-diazoacetate (0.48 g) as a bright yellow solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated onto silica gel
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-58abd92df448498eaeb2ec5ca9a9be3f
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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