HCID 69733903, compound → HCID 86585911, compound

HRID 488364Notes

Reaction equation

HRID 488364 reaction equation
[CH3:1][C:2]([CH3:35])([O:4][C:5]([NH:7][CH2:8][C@@H:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH2:21][N:20](C(OCC2C=CC=CC=2)=O)[CH2:19][CH2:18]3)[CH2:10]1)=[O:6])[CH3:3]>CO.[OH-].[OH-].[Pd+2]>[O:14]=[C:12]1[N:11]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:10][C@H:9]([CH2:8][NH:7][C:5](=[O:6])[O:4][C:2]([CH3:3])([CH3:1])[CH3:35])[O:13]1

Participants

4

Reactant 1

HCID 69733903HCID 69733903, compound

Product 1

HCID 86585911HCID 86585911, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of phenylmethyl 6-[(5S)-5-[[[(1,1-dimethylethoxy)carbonyl]amino]-methyl]-2-oxo-3-oxazolidinyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Step 1, 1.11 g, 2.31 mmol) and 20% Pd(OH)2/C (324 mg) in MeOH (23 mL) in a Parr bottle is shaken under 20 psi H2 for 1.25 hr. The resulting mixture is filtered through Celite to remove the catalyst, and the filtrate is concentrated under reduced pressure to give a quantitative yield of the product as an amorphous solid which is used without further purification. 1H NMR (400 MHz, CD3OD) δ 7.35 (bd, 1H), 7.31 (s, 1H), 7.08 (d, 1H), 4.75 (m, 1H), 4.14 (t, 1H), 3.97 (s, 2H), 3.87 (m, 1H), 3.42 (m, 2H), 3.11 (m, 2H), 2.87 (m, 2H), 1.42 (s, 9H); MS (ESI+) for C18H25N3O4 m/z 348 (M+H)30.

Workup

  1. filtrationThe resulting mixture is filtered through Celite
  2. customto remove the catalyst
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-695147de20c94a70bf8937709f64b383
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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