HCID 69734019, compound → HCID 69734604, compound

HRID 488358Notes

Reaction equation

HRID 488358 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][N:17](C(OCC2C=CC=CC=2)=O)[CH2:16][CH2:15]3)[CH2:7]1)(=[O:3])[CH3:2]>CO.C1COCC1.[OH-].[OH-].[Pd+2]>[CH2:18]1[C:19]2[C:14](=[CH:13][C:12]([N:8]3[CH2:7][C@H:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])[O:10][C:9]3=[O:11])=[CH:21][CH:20]=2)[CH2:15][CH2:16][NH:17]1

Participants

5

Reactant 1

HCID 69734019HCID 69734019, compound

Product 1

HCID 69734604HCID 69734604, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of phenylmethyl 6-[(5S)-5-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Step 5, 1.71 g, 4.04 mmol) and 20% Pd(OH)2/C (567 mg) in MeOH (40 mL) in a Parr bottle is shaken under 20 psi H2 for 1 hr. The resulting slurry is then diluted with MeOH (100 mL) and THF (100 mL), filtered through Celite to remove the catalyst, and concentrated under reduced pressure to give a quantitative yield of the title compound as an amorphous solid which is used without further purification. 1H NMR (400 MHz, CD3OD) δ 7.36 (bd, 1H), 7.31 (s, 1H), 7.08 (d, 1H), 4.78 (m, 1H), 4.14 (t, 1H), 3.98 (s, 2H), 3.82 (dd, 1H), 3.57 (m, 2H), 3.13 (m, 2H), 2.88 (m, 2H), 1.98 (s, 3H); MS (ESI+) for C15H19N3O3 m/z 290 (M+H)+.

Workup

  1. filtrationfiltered through Celite
  2. customto remove the catalyst
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1e91a9effd74b55bd642e6b746acacc
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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