tert-Butyl acrylate → HCID 53972944, compound

HRID 850681Notes

Reaction equation

HRID 850681 reaction equation
[NH2:1][CH2:2][C@H:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([CH3:26])([CH3:25])[C:15]([N:17]3[CH2:22][CH:21]4[CH2:23][CH2:24][CH:18]3[CH2:19][CH2:20]4)=[O:16])[CH:12]=2)[NH:7][C:6]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)[CH3:4].[C:35]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])(=[O:38])[CH:36]=[CH2:37]>>[C:40]([O:39][C:35](=[O:38])[CH2:36][CH2:37][NH:1][CH2:2][C@H:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([CH3:26])([CH3:25])[C:15]([N:17]3[CH2:22][CH:21]4[CH2:23][CH2:24][CH:18]3[CH2:19][CH2:20]4)=[O:16])[CH:12]=2)[NH:7][C:6]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)[CH3:4])([CH3:43])([CH3:42])[CH3:41]

Participants

3

Reactant 2

HCID 15458tert-Butyl acrylateHCID 9846936HCID 9846936, compound

Product 1

HCID 53972944HCID 53972944, compound

Procedure

To a solution of (S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(2-aza-bicyclo[2.2.2]oct-2-yl)-2-methylpropan-1-one (248.6 mg in 2.1 mL absolute ethanol) was added 0.080 mL tert-butyl acrylate and the mixtureheated to 70° C. on an oil bath. After 3 hours, the mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (methylene chloride:methanol, 94:6) to give the title compound (232 mg).

Workup

  1. custommixtureheated to 70° C.
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (methylene chloride:methanol, 94:6)

Sources & evidence

ORD record
ord-3239278834fd44ff9b5d9ecd76a61d80
Source dataset
uspto-grants-2000_01
Patent number
US06017944

Reaction notes

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