HCID 178502362, compound → HCID 86699510, compound

HRID 535120Notes

Reaction equation

HRID 535120 reaction equation
COC([NH:5][C@H](C(N1CCC[C@H]1C1NC=C(C2C=CC(C3C=CC(C4N=C([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]5C=CC=CC=5)=[O:49])NC=4)=CC=3)=CC=2)N=1)=O)C(C)C)=O.[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]>>[S:43]1[C:42]2([CH2:47][CH2:39][N:40]([C:48]([O-:50])=[O:49])[CH2:41]2)[S:46][CH2:45][CH2:44]1.[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 86699510HCID 86699510, compoundYield 87%HCID 178502367HCID 178502367, compound

Procedure

Phenylmethyl (8S)-8-(4-{4′42-((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-22c73103203449dd8cd2685b71b879ff
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

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