HCID 69733903, compound → HCID 86585911, compound
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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.