HCID 178502361, compound → HCID 178502363, compound

HRID 535119Notes

Reaction equation

HRID 535119 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[C:17]1[NH:18][CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[N:35]=[C:36]([C@@H:39]5[CH2:43][C:42]6([O:48][CH2:47][CH2:46][CH2:45][O:44]6)[CH2:41][N:40]5C(OCC5C=CC=CC=5)=O)[NH:37][CH:38]=4)=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)[N:21]=1)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4]>C(O)C.[Pd]>[CH2:41]1[C:42]2([O:48][CH2:47][CH2:46][CH2:45][O:44]2)[CH2:43][C@@H:39]([C:36]2[NH:37][CH:38]=[C:34]([C:31]3[CH:30]=[CH:29][C:28]([C:25]4[CH:26]=[CH:27][C:22]([C:20]5[N:21]=[C:17]([C@@H:13]6[CH2:14][CH2:15][CH2:16][N:12]6[C:10]([C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH:7]([CH3:9])[CH3:8])=[O:11])[NH:18][CH:19]=5)=[CH:23][CH:24]=4)=[CH:33][CH:32]=3)[N:35]=2)[NH:40]1

Participants

4

Reactant 1

HCID 178502361HCID 178502361, compound2×

Product 1

HCID 178502363HCID 178502363, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Phenylmethyl (3S)-3-(4-{4′-[2-((2S)-1-{N-[(methyloxy)carbonyl]-L-valyl}-2-pyrrolidinyl)-1H-imidazol-4-yl]-4-biphenylyl}-1H-imidazol-2-yl)-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate (Intermediate 22) (1.44 g, 1.83 mmol) was hydrogenated in ethanol (100 mL) with balloon under the catalysis of Pd/C for 20 hrs to give methyl [(1S)-1-({(2S)-2-[4-(4′-{2-[(3S)-6,10-dioxa-2-azaspiro[4.5]dec-3-yl]-1H-imidazol-4-yl]-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}carbonyl)-2-methylpropyl]carbamate (Intermediate 19). ES LC-MS m/z=654.4 (M+H)+.

Sources & evidence

ORD record
ord-50195ccded05417c94e4f823d10166b0
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

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