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

HRID 1423078ノート

反応式

HRID 1423078 の反応式
[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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-bfb2b5135f51465ab44abbdc0ce8a51b
出典データセット
uspto-grants-2015_01
特許番号
US08927546B2

反応ノート

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