Hydrochloric Acid → 1-Benzyl-3(S)-(2'-methylbenzyl)-piperazine-2,5-dione

HRID 1423078노트

반응식

HRID 1423078 반응식
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])([O:3]C(C)(C)C)=O.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.C(OC(=O)[CH2:44][NH:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>CN(C=O)C.CCOC(C)=O>[CH2:46]([N:45]1[CH2:44][C:1](=[O:3])[NH:8][C@@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:18]1=[O:20])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 80908N-Benzylglycine ethyl esterHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2761468Boc-L-2-Methylphenylalanine

생성물 1

HCID 668249411-Benzyl-3(S)-(2'-methylbenzyl)-piperazine-2,5-dione수율 139.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of Boc-2-methyl-L-phenylalanine (2.79 g, 10 mmol) in DMF (25 mL) was treated sequentially with HOBt (2.03 g, 15 mmol), diisopropylethylamine (4.35 mL, 25 mmol), N-benzylglycine ethyl ester (2.03 mL, 11 mmol), and HBTU (5.69 g, 15 mmol). The resulting solution was allowed to stir for 16 h after which time the mixture was poured onto a mixture of a 1 N aqueous HCl (50 mL) solution and EtOAc (50 mL). The organic portion was separated and further extracted with a saturated aqueous NaHCO3 solution (50 mL) follow by brine (50 mL). The organic phase was dried over MgSO4, filtered and evaporated to an oil, which was purified by silica gel flash chromatography with 20% then 30% EtOAc/hexanes as eluant to afford titled compound as a solid (4.31 g, 95%). LC/MS (Method A) 7.43 min, [M+1]+ 455.

후처리

  1. customThe organic portion was separated
  2. extractionfurther extracted with a saturated aqueous NaHCO3 solution (50 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to an oil, which
  6. customwas purified by silica gel flash chromatography with 20%

출처 및 근거

ORD 기록
ord-bfb2b5135f51465ab44abbdc0ce8a51b
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927546B2

반응 노트

불러오는 중…