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

HRID 523185Notes

Reaction equation

HRID 523185 reaction equation
[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]

Participants

6

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-98529f86d4f14b249cb242983ea3c6c9
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Reaction notes

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