HCID 178487960, compound → HCID 178487969, compound

HRID 633804Notes

Reaction equation

HRID 633804 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH:15]2[CH:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[N:28]=4)[N:23]=[CH:22][C:21]=3[O:32]CC3C=CC=CC=3)OC(=O)[O:16]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:41])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][CH:15]([OH:16])[CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[N:28]=3)[N:23]=[CH:22][C:21]=2[OH:32])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 178487960HCID 178487960, compound

Product 1

HCID 178487969HCID 178487969, compoundYield 68.3%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on activated carbon (976 mg, 0.91 mmol, 0.3 eq) is added at room temperature to a stirred solution of {trans-4-[5-(3-benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-2-oxo-[1,3]dioxolan-4-ylmethyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.70 g, 3.02 mmol, 1.0 eq) in methanol (200 mL), followed by several drops of triethylamine. The resulting mixture is stirred under hydrogen flow (1 bar) at room temperature for 1 hour. The catalyst is then removed by filtration and the solution is concentrated to afford {trans-4-[2-hydroxy-3-(3-hydroxy-6-methoxy-[1,5]naphthyridin-4-yl)-propyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (890 mg, 68% yield).

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-7b7c7c77ef0a4dddb1656f4a9c7d5065
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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