Sodium Carbonate → N1-((S)-1-(4-bromophenyl)ethyl)-5-methyl-3-phenylhex-5-ene-1,3-diamine

HRID 1523258ノート

反応式

HRID 1523258 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][C:20]([NH:31][S@@](C(C)(C)C)=O)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][C:22]([CH3:24])=[CH2:23])C(=O)OC(C)(C)C)[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][CH2:18][CH2:19][C:20]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([NH2:31])[CH2:21][C:22]([CH3:24])=[CH2:23])[CH3:9])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 10340Sodium CarbonateHCID 59627246tert-butyl (S)-1-(4-bromophenyl)ethyl(3-((R)-1,1-dimethylethylsulfinamido)-5-methyl-3-phenylhex-5-enyl)carbamate

生成物 1

HCID 59627223N1-((S)-1-(4-bromophenyl)ethyl)-5-methyl-3-phenylhex-5-ene-1,3-diamine収率 70%

試薬・触媒・溶媒 1

HCID 204431481,4-Dioxane hydrochloride溶媒

反応条件

温度
0 °C

実験手順

A mixture of tert-butyl (S)-1-(4-bromophenyl)ethyl(3-((R)-1,1-dimethylethylsulfinamido)-5-methyl-3-phenylhex-5-enyl)carbamate (6.5 g, 0.011 mol) in HCl/dioxane (70 mL) was stirred for 1 hour at 0° C. The mixture was concentrated to give the residue, which was treated with satd aq Na2CO3. The resulting mixture was extracted with EtOAc, and the combined organic layer was concentrated to afford crude N1—((S)-1-(4-bromophenyl)ethyl)-5-methyl-3-phenylhex-5-ene-1,3-diamine (2.97 g, 70%), which was used for the next step without purification.

後処理

  1. concentrationThe mixture was concentrated
  2. customto give the residue, which
  3. extractionThe resulting mixture was extracted with EtOAc
  4. concentrationthe combined organic layer was concentrated

出典と根拠

ORDレコード
ord-14d9d37947034348b849e115f3731500
出典データセット
uspto-grants-2015_07
特許番号
US09079861B2

反応ノート

読み込み中…