HCID 69094055, compound → HCID 67509081, compound

HRID 1770722Notes

Reaction equation

HRID 1770722 reaction equation
C(OC(=O)[NH:10][C:11]([CH3:30])([CH2:13][CH2:14][S:15]([CH2:18][C@@H:19]1[C@@H:24]([OH:25])[C@H:23]([OH:26])[C@@H:22]([OH:27])[C@@H:21]([O:28][CH3:29])[O:20]1)(=[O:17])=[O:16])[CH3:12])C1C=CC=CC=1>CO.[Pd]>[NH2:10][C:11]([CH3:30])([CH3:12])[CH2:13][CH2:14][S:15]([CH2:18][C@@H:19]1[C@@H:24]([OH:25])[C@H:23]([OH:26])[C@@H:22]([OH:27])[C@@H:21]([O:28][CH3:29])[O:20]1)(=[O:16])=[O:17]

Participants

4

Reactant 1

HCID 69094055HCID 69094055, compound

Product 1

HCID 67509081HCID 67509081, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, 175 mg of 10% Pd on carbon was added to a solution of benzyl(2-methyl-4-((((2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl)sulfonyl)butan-2-yl)carbamate (700 mg, 1.5 mmol) in 5 mL of methanol. The resultant mixture was degassed and placed under a hydrogen atmosphere, stirring for 3 hours. The suspension was filtered through a pad of celite, washing with methanol, and the filtrate was concentrated under reduced pressure to give ca 496 mg of white foam (quantitative yield). 1H NMR (400 MHz, CD3OD) δ 1.19 (s, 6H), 1.90-1.95 (m, 2H), 3.13-3.18 (dd, J=8.9, 9.9 Hz, 1H), 3.21-3.30 (m, 2H), 3.4-3.43 (m, 3H), 3.48 (s, 3H), 3.61-3.66 (t, J=9.2 Hz, 1H), 4.04-4.10 (m, 1H), 4.69-4.70 (d, J=3.7 Hz, 1H). 13C NMR (100 MHz, MeOD) δ 27.6, 27.7, 34.8, 48.8, 50.8, 53.9, 54.9, 67.3, 71.9, 72.8, 73.3, 100.1. LRMS (ESI/APCI) m/z 328 [M+H]+.

Workup

  1. customThe resultant mixture was degassed
  2. filtrationThe suspension was filtered through a pad of celite
  3. washwashing with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e1cfb8cdd924f31b8066ae9421f8abb
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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