Bromide ion → (S)-2-(4-bromobenzyl)amino-3-methylbutyric acid

HRID 12593

반응식

HRID 12593 반응식
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C(N([CH:15]([CH3:17])[CH3:16])CC)(C)C.[Br-:18].[OH-].[Na+]>CN(C=O)C.O.C1(C)C=CC=CC=1>[Br:18][C:16]1[CH:15]=[CH:17][C:3]([CH2:4][NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])=[CH:2][CH:6]=1

참가 물질

8

반응물 4

HCID 259Bromide ionHCID 6287L-ValineHCID 14798Sodium HydroxideHCID 81531Diisopropylethylamine

생성물 1

HCID 11673643(S)-2-(4-bromobenzyl)amino-3-methylbutyric acid수율 153.4%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
22.5 °C

실험 절차

52 mL (0.21 mol) of N,O-bistrimethylsilylacetamide is added under nitrogen atmosphere to a mixture made up of 23.5 g (0.20 mol) of L-valine and 38.5 mL (0.22 mol) of diisopropylethylamine in 12.5 mL of DMF. After 1 h at 80° C. the suspension changes to a clear solution. Then, in portions and controlling exothermy, 50 g (0.20 mol) of 4-bromobenzylo bromide is added and left to react at 80° C. for 2 h. The mixture is cooled to 20-25° C., 250 mL of toluene and a solution made up of 250 mL of water and 80 mL of NaOH 40% are added. The resulting aqueous phase is washed twice with 100 mL of AcOEt, the remains of solvent distilled and taken to pH 6-7 with HCl 3N. The solid obtained is filtered with 250 mL of IPA to give 43.9 g (76.5%) of N-(4-bromobenzyl)-L-valine.

후처리

  1. additionis added
  2. waitleft
  3. customto react at 80° C. for 2 h
  4. additionare added
  5. washThe resulting aqueous phase is washed twice with 100 mL of AcOEt
  6. distillationthe remains of solvent distilled
  7. customThe solid obtained
  8. filtrationis filtered with 250 mL of IPA

출처 및 근거

ORD 기록
ord-145a239c04c24a43b4d3485f843fcd6d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728021B2

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