HCID 86612333, compound → HCID 16226508, compound
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3[C:27]([O:29][CH2:30][P:31]([O:41]CC1C=CC=CC=1)([O:33]CC1C=CC=CC=1)=[O:32])=[O:28])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2]>[OH-].[OH-].[Pd+2].CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3[C:27]([O:29][CH2:30][P:31](=[O:32])([OH:41])[OH:33])=[O:28])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
1.5 g (2.25 mmol) of the compound from Example 21C was added to a mixture of 0.3 g 20% Pd(OH)2/C and 150 mL methanol in a stainless steel autoclave. The reactor was sealed and flushed with nitrogen, and then it was pressurized with hydrogen (60 psi). The mixture was stirred at ambient temperature for 90 minutes. Product precipitated, added 150 mL tetrahydrofuran to redissolve, catalyst was filtered off, washed with methanol and tetrahydrofuran, and the filtrate was concentrated to provide 1.08 g (99%) of the title compound. MS (ESI) m/z: 485.21 [M−H]− 1H NMR (DMSO-d6) δ: 1.28 (s, 9H), 1.81-1.88 (m, 1H), 2.42-2.48 (m, 1H), 2.79-2.87 (m, 1H), 2.91-3.01 (m, 1H), 4.56 (d, 2H), 5.16 (q, 1H), 6.69 (d, 1H), 7.27 (s, 2H), 7.31 (s, 1H), 7.50 (t, 1H), 7.72 (d, 1H), 7.89 (d, 1H), 8.43 (s, 1H), 8.85 (s, 1H).
Workup
- customThe reactor was sealed
- customflushed with nitrogen
- customProduct precipitated
- additionadded 150 mL tetrahydrofuran
- dissolutionto redissolve
- filtrationcatalyst was filtered off
- washwashed with methanol and tetrahydrofuran
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-baa4cfd95deb4324b8ed777b092b1fb5
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232309B2
Reaction notes
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