(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid → HCID 89917738, compound

HRID 1751552Notes

Reaction equation

HRID 1751552 reaction equation
COC(N[C@@H](C(C)C)C(N1CC(=O)C[C@H]1C(OCC1C=CC=CC=1)=O)=O)=O.Cl.Cl.Cl.[F:31][C:32]1([F:85])[C:44]2[CH:43]=[C:42]([C:45]3[CH:46]=[CH:47][C:48]4[N:52]=[C:51]([C@@H:53]5[C@H:58]6[CH2:59][C@@H:55]([CH2:56][CH2:57]6)[N:54]5[C:60](=[O:73])[C@H:61]([NH:68][C:69](=[O:72])[O:70][CH3:71])[C:62]5[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=5)[NH:50][C:49]=4[CH:74]=3)[CH:41]=[CH:40][C:39]=2[C:38]2[C:33]1=[CH:34][C:35]([C:75]1[NH:79][C:78]([C@@H:80]3[CH2:84][CH2:83][CH2:82][NH:81]3)=[N:77][CH:76]=1)=[CH:36][CH:37]=2.[CH3:86][O:87][C:88]([NH:90][C@@H:91]([CH:95]1[CH2:100][CH2:99][O:98][CH2:97][CH2:96]1)[C:92](O)=[O:93])=[O:89].Cl.O=C1CN[C@H](C(OCC2C=CC=CC=2)=O)C1.COC(N[C@@H](C(C)C)C(O)=O)=O>>[CH3:71][O:70][C:69](=[O:72])[NH:68][C@H:61]([C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)[C:60]([N:54]1[C@H:53]([C:51]2[NH:50][C:49]3[CH:74]=[C:45]([C:42]4[CH:41]=[CH:40][C:39]5[C:38]6[C:33](=[CH:34][C:35]([C:75]7[NH:79][C:78]([C@@H:80]8[CH2:84][CH2:83][CH2:82][N:81]8[C:92](=[O:93])[C@@H:91]([NH:90][C:88]([O:87][CH3:86])=[O:89])[CH:95]8[CH2:100][CH2:99][O:98][CH2:97][CH2:96]8)=[N:77][CH:76]=7)=[CH:36][CH:37]=6)[C:32]([F:31])([F:85])[C:44]=5[CH:43]=4)[CH:46]=[CH:47][C:48]=3[N:52]=2)[C@H:58]2[CH2:59][C@H:55]1[CH2:56][CH2:57]2)=[O:73]

Participants

6

Reactant 5

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 59264488(S)-2-(Methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acidHCID 59610664(S)-benzyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-4-oxopyrrolidine-2-carboxylateHCID 86648889HCID 86648889, compoundHCID 131733617HCID 131733617, compound

Product 1

HCID 89917738HCID 89917738, compound

Procedure

The title compound was prepared according to the method employed to prepare (S)-benzyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-4-oxopyrrolidine-2-carboxylate, except that methyl (R)-2-((1R,3S,4R)-3-(6-(9,9-difluoro-7-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-2-oxo-1-phenylethylcarbamate 3HCl salt and (S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid were used instead of (S)-benzyl 4-oxopyrrolidine-2-carboxylate hydrochloride and (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid. MS (ESI) m/z 939.92 [M+H]+. (34 mg, 23%).

Sources & evidence

ORD record
ord-45882e036b934a4e8b9e4839ff0d676f
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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