Lithium Hydroxide → (2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoic acid

HRID 523183Notes

Reaction equation

HRID 523183 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:14]([O:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[CH2:15][CH3:16])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[Li+].[OH-]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:14]([O:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[CH2:15][CH3:16])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 118415151HCID 118415151, compound

Product 1

HCID 90118077(2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round-bottom flask equipped with a stir bar was added (2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoate (1.06 g, 3.36 mmol), THF (10 mL) and MeOH (10 mL). To the solution was added aq. LiOH (1.0 M, 5.04 mL). The mixture was stirred for 16 h at room temperature. The mixture was concentrated in vacuo, and the resulting aqueous solution was acidified with aq HCl (1.0 M) and then transferred to a separatory funnel. The solution was twice extracted with EtOAc and the combined organics were dried over MgSO4; filtered; then concentrated in vacuo to afford (2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoic acid as a colorless solid foam (1.00 g, 99% yield).

Workup

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

Sources & evidence

ORD record
ord-342c7339f50245fc9a6b136748be8ff1
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Reaction notes

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