Lithium Hydroxide → 2-(2-(((Benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoic acid

HRID 627579Notes

Reaction equation

HRID 627579 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:25][C:26]#[CH:27])[C:13]([NH:15][CH:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:17]([O:19]C)=[O:18])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:25][C:26]#[CH:27])[C:13]([NH:15][CH:16]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:17]([OH:19])=[O:18])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 78106115Methyl 2-(2-(((benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoate

Product 1

HCID 781061162-(2-(((Benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoic acidYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of compound 3 (10.85 g; 29 mmol) in dry THF (100 mL) kept in an ice bath was treated with a solution of 1M lithium hydroxide (100 mL) and stirred for 4 h at 0° C. until the starting material disappeared (as shown by TLC). The solvent was removed and the residue was diluted with water (25 mL). The pH of the aqueous solution was adjusted to ˜2 with 5% HCl and the solution was extracted with ethyl acetate (2×250 mL) and washed with brine (100 mL). The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated, yielding a crude product which was purified by flash chromatography (silica gel; hexane/ethyl acetate 50:50) to give 4 as a white solid (8.8 g; 84% yield). 1H NMR (DMSO-d6) δ 8.1 (s, 1H), 7.5 (s, 1H), 7.3 (m, 5H), 5.0 (s, 2H), 4.4 (m, 1H), 4.2 (m, 1H), 2.8 (s, 1H), 2.5 (m, 1H), 2.4 (m, 1H), 1.6 (m, 2H), 1.4 (m, 1H), 0.8 (d, 6H)

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with water (25 mL)
  3. extractionthe solution was extracted with ethyl acetate (2×250 mL)
  4. washwashed with brine (100 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customyielding a crude product which
  10. customwas purified by flash chromatography (silica gel; hexane/ethyl acetate 50:50)

Sources & evidence

ORD record
ord-1879fe675820486ab6c7a59ac35662dc
Source dataset
uspto-grants-2016_04
Patent number
US09309284B2

Reaction notes

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