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

HRID 1523258노트

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HRID 1523258 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 204431481,4-Dioxane hydrochloride용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-14d9d37947034348b849e115f3731500
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079861B2

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