HCID 178502362, compound → HCID 178502362, compound

HRID 1748855Notes

Reaction equation

HRID 1748855 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[CH2:47][C:42]6([S:46][CH2:45][CH2:44][S:43]6)[CH2:41][N:40]5[C:48]([O:50][CH2:51][C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)=[O:49])[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].[CH3:58][CH:59]([CH3:115])[C@H:60]([NH:110][C:111]([O:113][CH3:114])=[O:112])[C:61]([N:63]1[CH2:67][CH2:66][CH2:65][C@H:64]1[C:68]1[NH:69][CH:70]=[C:71]([C:73]2[CH:78]=[CH:77][C:76]([C:79]3[CH:84]=[CH:83][C:82]([C:85](=[O:109])[CH2:86][NH:87][C:88]([C@@H:90]4[CH2:98][C:93]5([S:97][CH2:96][CH2:95][S:94]5)[CH2:92][N:91]4[C:99]([O:101][CH2:102][C:103]4[CH:108]=[CH:107][CH:106]=[CH:105][CH:104]=4)=[O:100])=[O:89])=[CH:81][CH:80]=3)=[CH:75][CH:74]=2)[N:72]=1)=[O:62]>>[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:23]=[CH:24][C:25]([C:28]3[CH:29]=[CH:30][C:31]([C:34]4[N:35]=[C:36]([C@@H:39]5[CH2:47][C:42]6([S:46][CH2:45][CH2:44][S:43]6)[CH2:41][N:40]5[C:48]([O:50][CH2:51][C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)=[O:49])[NH:37][CH:38]=4)=[CH:32][CH:33]=3)=[CH:26][CH:27]=2)[N:21]=1)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].[CH3:58][CH:59]([CH3:115])[C@H:60]([NH:110][C:111]([O:113][CH3:114])=[O:112])[C:61]([N:63]1[CH2:67][CH2:66][CH2:65][C@H:64]1[C:68]1[NH:69][CH:70]=[C:71]([C:73]2[CH:74]=[CH:75][C:76]([C:79]3[CH:84]=[CH:83][C:82]([C:85](=[O:109])[CH2:86][NH:87][C:88]([C@@H:90]4[CH2:98][C:93]5([S:97][CH2:96][CH2:95][S:94]5)[CH2:92][N:91]4[C:99]([O:101][CH2:102][C:103]4[CH:108]=[CH:107][CH:106]=[CH:105][CH:104]=4)=[O:100])=[O:89])=[CH:81][CH:80]=3)=[CH:77][CH:78]=2)[N:72]=1)=[O:62].[C:51]([O-:62])(=[O:50])[CH3:52].[NH4+:5]

Participants

5

Reactant 2

HCID 178502362HCID 178502362, compoundHCID 178502367HCID 178502367, compound

Product 3

HCID 517165Ammonium AcetateHCID 178502362HCID 178502362, compoundYield 87%HCID 178502367HCID 178502367, compound

Procedure

Phenylmethyl (8S)-8-(4-{4′-[2-((2S)-1-{N-[(methyloxy)carbonyl]-L-valyl}-2-pyrrolidinyl)-1H-imidazol-4-yl]-4-biphenylyl}-1H-imidazol-2-yl)-1,4-dithia-7-azaspiro[4.4]nonane-7-carboxylate (Intermediate 38) (497 mg, 87%) was obtained from phenylmethyl (8S)-8-({[2-(4′-{2-[(2S)-1-((2S)-3-methyl-2-{[(methyloxy)carbonyl]amino}butanoyl)-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-2-oxoethyl]amino}carbonyl)-1,4-dithia-7-azaspiro[4.4]nonane-7-carboxylate (Intermediate 37) (584 mg, 0.71 mmol) and ammonium acetate (546 mg, 7.1 mmol), following the similar procedure outlined in the preparation of Intermediate (22). ES LC-MS m/z=806.4 (M+H).

Sources & evidence

ORD record
ord-b7f8ea4a878347a6bbf23883ef1ed8ee
Source dataset
uspto-grants-2015_10
Patent number
US09150587B2

Reaction notes

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