HCID 86678444, compound → HCID 86678445, compound

HRID 1625537Notes

Reaction equation

HRID 1625537 reaction equation
[C:1]([O:5][C:6]([N:8]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:9]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:10][CH2:11][CH:12]([OH:22])[C:13]#[C:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@@H:9]([CH2:10][CH2:11][CH:12]([OH:22])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86678444HCID 86678444, compound

Product 1

HCID 86678445HCID 86678445, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 25-mL round bottom (RB) flask was purged with nitrogen and charged with (7S)-di-tert-butyl 7-(bis(tert-butoxycarbonyl)amino)-4-hydroxyoct-2-ynedioate (0.04 g, 0.08 mmol), ethyl acetate (5 mL) and 5% palladium on carbon (˜2.0 mg dry weight). The RB flask was evacuated, charged with hydrogen gas in a balloon (to a pressure of 13 psi or approximately 1.0 atmosphere pressure) and stirred for an overnight at room temperature. After this time, the hydrogen was evacuated and nitrogen charged into the RB flask. The catalyst was removed by filtration through a pad of Celite 545 and the filter cake washed with ethyl acetate (10 mL). The filtrate was concentrated under reduced pressure to afford (2S)-di-tert-butyl 2-(bis(tert-butoxycarbonyl)amino)-5-hydroxyoctanedioate (diastereomeric mixture, 0.04 g, 99.3% yield) as an oil. 1H NMR (CDCl3) δ ppm: 4.73 (m, 1H), 3.63 (m, 1H), 2.37 (m, 2H), 2.27-1.56 (m, 6H), 1.51 (s, 18H), 1.45 (2s, 18H). 13C NMR (CDCl3) d ppm: 173.60, 173.58, 170.01, 169.75, 152.58, 152.48, 82.86, 82.82, 81.28, 81.25, 80.42, 80.40, 71.19, 70.65, 58.92, 58.68, 34.37, 34.15, 32.30, 32.22, 32.15, 32.05, 28.07, 28.02, 27.94, 25.69 and 25.55. MS (ESI+): 540 (M+Na)+.

Workup

  1. customA 25-mL round bottom (RB) flask was purged with nitrogen
  2. customThe RB flask was evacuated
  3. additioncharged with hydrogen gas in a balloon (to a pressure of 13 psi or approximately 1.0 atmosphere pressure) and
  4. customAfter this time, the hydrogen was evacuated
  5. additionnitrogen charged into the RB flask
  6. customThe catalyst was removed by filtration through a pad of Celite 545
  7. washthe filter cake washed with ethyl acetate (10 mL)
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa7b601c1d4043ee93971bfe32d81ab0
Source dataset
uspto-grants-2014_07
Patent number
US08784774B2

Reaction notes

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