HCID 126489439, compound → HCID 118194673, compound

HRID 1770376Notes

Reaction equation

HRID 1770376 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][CH2:21][CH2:22][C@H:23]([O:33][CH2:34][CH2:35][CH3:36])[C@H:24]([C@@H:30]([OH:32])[CH3:31])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:10]([O:12]CC1C=CC=CC=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][CH2:21][CH2:22][C@H:23]([O:33][CH2:34][CH2:35][CH3:36])[C@H:24]([C@@H:30]([OH:32])[CH3:31])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:10]([OH:12])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 126489439HCID 126489439, compound

Product 1

HCID 118194673HCID 118194673, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S,6S,7S)-benzyl 2-((tert-butoxycarbonyl)amino)-7-((S)-1-hydroxyethyl)-10-methyl-6-propoxyundecanoate (815 mg, 1.61 mmol) and 10% Pd/C (85 mg, 0.803 mmol) in THF (5.35 mL) was stirred under a hydrogen atmosphere (balloon pressure) at room temperature for 4 h. The hydrogen was removed using a stream of N2 and the reaction was filtered through a plug of Celite®. The plug was washed with DCM (2×5 mL) and the combined filtrate and washes were concentrated to dryness under reduced pressure to afford the title compound (660 mg, 1.58 mmol, 98%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 5.14 (d, J=8.2 Hz, 1H), 4.36-4.26 (m, 1H), 3.95-3.83 (m, 1H), 3.63-3.52 (m, 1H), 3.49-3.41 (m, 1H), 3.37-3.27 (m, 1H), 1.93-1.81 (m, 2H), 1.79-0.80 (m, 33H) (carboxylic acid peak is very broad (not listed) and alcohol proton is not visible); 13C NMR (101 MHz, CDCl3) δ 175.98, 155.52, 82.43, 79.93, 71.50, 69.42, 53.26, 45.32, 37.36, 32.61, 28.69, 28.31, 28.26, 25.17, 23.16, 22.66, 22.39, 21.82, 10.63; ESIMS m/z 416 ([M−H]−).

Workup

  1. customThe hydrogen was removed
  2. filtrationthe reaction was filtered through a plug of Celite®
  3. washThe plug was washed with DCM (2×5 mL)
  4. concentrationthe combined filtrate and washes were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-351cb079c0fe46d19dd244703fc652c9
Source dataset
uspto-grants-2016_02
Patent number
US09247741B2

Reaction notes

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