Lithium Hydroxide → (2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid

HRID 523170노트

반응식

HRID 523170 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:22]([CH3:30])[CH2:23][CH:24]([CH3:29])[CH2:25][CH2:26][CH:27]=[CH2:28])[C:10]([N:12]1[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]1[C:18]([O:20]C)=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:22]([CH3:30])[CH2:23][CH:24]([CH3:29])[CH2:25][CH2:26][CH:27]=[CH2:28])[C:10]([N:12]1[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]1[C:18]([OH:20])=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86683197HCID 86683197, 화합물

생성물 1

HCID 86683196(2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid수율 84%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a 250 mL round-bottom flask equipped with a large stir bar was added (2S,4R)-methyl 1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylate (10.9 g, 25.5 mmol), then THF (75 mL) and methanol (75 mL). To the stirred solution was added aq. lithium hydroxide (2.0 M, 38 mL, 77 mmol). The mixture was vigorously stirred for 1.5 h. The volatiles were removed organics were removed in vacuo and the resulting aqueous solution and solid residue was transfered to a 500 mL separatory funnel. The aqueous phase was adjusted to pH 2.5 using aqueous 2N HCl and was then extracted with EtOAc (3×100 mL). The combined organics were washed with aqueous sat. NaCl adjusted to pH 2.5 with aqueous HCl, dried over MgSO4; filtered; then concentrated in vacuo to afford (2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid as a colorless foam (8.82 g, 84%). MS: MS m/z 413.2 (M++1).

후처리

  1. customTo a 250 mL round-bottom flask equipped with a large stir bar
  2. customThe volatiles were removed organics
  3. customwere removed in vacuo
  4. customthe resulting aqueous solution and solid residue was transfered to a 500 mL separatory funnel
  5. extractionwas then extracted with EtOAc (3×100 mL)
  6. washThe combined organics were washed with aqueous sat. NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationthen concentrated in vacuo

출처 및 근거

ORD 기록
ord-9bf98bfa3b434561a325e676aab35087
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334279B2

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