(S)-benzyl 2-((2R,6R)-2,6-dimethyltetrahydro-2H-pyran-4-yl)-2-(methoxycarbonylamino)acetate → (S)-2-((2R,6R)-2,6-Dimethyltetrahydro-2H-pyran-4-yl)-2-((methoxycarbonyl)amino)acetic acid

HRID 525117Notes

Reaction equation

HRID 525117 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH:6]([C@H:8]([NH:19][C:20]([O:22][CH3:23])=[O:21])[C:9]([O:11]CC2C=CC=CC=2)=[O:10])[CH2:5][C@@H:4]([CH3:24])[O:3]1>CO.[Pd]>[CH3:1][C@@H:2]1[CH2:7][CH:6]([C@H:8]([NH:19][C:20]([O:22][CH3:23])=[O:21])[C:9]([OH:11])=[O:10])[CH2:5][C@@H:4]([CH3:24])[O:3]1

Participants

4

Reactant 1

HCID 86668465(S)-benzyl 2-((2R,6R)-2,6-dimethyltetrahydro-2H-pyran-4-yl)-2-(methoxycarbonylamino)acetate

Product 1

HCID 66746681(S)-2-((2R,6R)-2,6-Dimethyltetrahydro-2H-pyran-4-yl)-2-((methoxycarbonyl)amino)acetic acidYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-Benzyl 2-((2R,6R)-2,6-dimethyltetrahydro-2H-pyran-4-yl)-2-(methoxycarbonylamino)acetate (Cap-2, step e) (56 mg, 0.167 mmol) was dissolved in MeOH (4 mL) and then treated with 10% Pd/C (12 mg, 0.012 mmol). The reaction mixture was vacuum flushed with nitrogen (4×) and then with hydrogen (4×) and stirred under a balloon of hydrogen overnight. The reaction was filtered through Celite® and concentrated to yield (S)-2-((2R,6R)-2,6-dimethyltetrahydro-2H-pyran-4-yl)-2-(methoxycarbonylamino)acetic acid (Cap-2) (41 mg) as a colorless oil. 1H NMR (400 MHz, D4-MeOH) δ ppm 4.22 (quin, J=6.4 Hz, 1H), 4.04-4.11 (m, 1H), 3.78-3.87 (m, 1H), 3.66 (s, 3H), 2.26-2.39 (m, 1H), 1.63 (d, J=13.1 Hz, 1H), 1.51-1.60 (m, 1H), 1.42-1.49 (m, 1H), 1.27 (d, J=7.0 Hz, 3H), 1.11 (d, J=6.3 Hz, 3H), 0.97-1.08 (m, 1H).

Workup

  1. customflushed with nitrogen (4×)
  2. filtrationThe reaction was filtered through Celite®
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2715570da0ff43d798f0eda4b80aaffc
Source dataset
uspto-grants-2016_05
Patent number
US09340520B2

Reaction notes

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