Hydrochloric Acid → (2S,4R)-1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylic acid

HRID 523185ノート

反応式

HRID 523185 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:22]([O:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])[CH2:23][CH3:24])[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.[Li+].[OH-].Cl>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:22]([O:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])[CH2:23][CH3:24])[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90121388(2S,4R)-methyl 1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylate2 回

生成物 1

HCID 90118137(2S,4R)-1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a round-bottom flask equipped with a stir bar was added (2S,4R)-methyl 1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylate (all material from step 2, 1.53 g, 3.57 mmol), THF (10 mL) and MeOH (10 mL). To the solution was added aq. LiOH (1.0 M, 5.36 mL). The mixture was stirred at room temperatuer for 16 h; then was concentrated in vacuo to afford an aqueous solution. The solution was acidified with aq HCl (1M) and then transferred to a separatory funnel. The solution was twice extracted with EtOAc. The combined organics were dried over MgSO4; filtered; then concentrated in vacuo to afford (2S,4R)-1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylic acid as a white solid (1.28 g, 86% over two steps).

後処理

  1. customTo a round-bottom flask equipped with a stir bar
  2. concentrationthen was concentrated in vacuo
  3. customto afford an aqueous solution
  4. customtransferred to a separatory funnel
  5. extractionThe solution was twice extracted with EtOAc
  6. dry with materialThe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationthen concentrated in vacuo

出典と根拠

ORDレコード
ord-98529f86d4f14b249cb242983ea3c6c9
出典データセット
uspto-grants-2016_05
特許番号
US09334279B2

反応ノート

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