(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid → HCID 86708767, compound

HRID 1751549Notes

Reaction equation

HRID 1751549 reaction equation
COC(N[C@@H](C(C)C)C(N1CC(=O)C[C@H]1C(OCC1C=CC=CC=1)=O)=O)=O.[CH3:28][O:29][C:30]([NH:32][C@@H:33]([CH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)[C:34]([OH:36])=O)=[O:31].[F:43][C:44]1([F:99])[C:56]2[CH:55]=[C:54]([C:57]3[CH:58]=[CH:59][C:60]4[N:64]=[C:63]([C@@H:65]5[CH2:73][C:68]6([O:72][CH2:71][CH2:70][O:69]6)[CH2:67][N:66]5[C:74](=[O:87])[C@H:75]([NH:82][C:83](=[O:86])[O:84][CH3:85])[C:76]5[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=5)[NH:62][C:61]=4[CH:88]=3)[CH:53]=[CH:52][C:51]=2[C:50]2[C:45]1=[CH:46][C:47]([C:89]1[NH:93][C:92]([C@@H:94]3[CH2:98][CH2:97][CH2:96][NH:95]3)=[N:91][CH:90]=1)=[CH:48][CH:49]=2.Cl.O=C1CN[C@H](C(OCC2C=CC=CC=2)=O)C1.COC(N[C@@H](C(C)C)C(O)=O)=O>>[CH3:85][O:84][C:83](=[O:86])[NH:82][C@H:75]([C:76]1[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=1)[C:74]([N:66]1[C@H:65]([C:63]2[NH:62][C:61]3[CH:88]=[C:57]([C:54]4[CH:53]=[CH:52][C:51]5[C:50]6[C:45](=[CH:46][C:47]([C:89]7[NH:93][C:92]([C@@H:94]8[CH2:98][CH2:97][CH2:96][N:95]8[C:34](=[O:36])[C@@H:33]([NH:32][C:30]([O:29][CH3:28])=[O:31])[CH:37]8[CH2:42][CH2:41][O:40][CH2:39][CH2:38]8)=[N:91][CH:90]=7)=[CH:48][CH:49]=6)[C:44]([F:43])([F:99])[C:56]=5[CH:55]=4)[CH:58]=[CH:59][C:60]=3[N:64]=2)[CH2:73][C:68]2([O:69][CH2:70][CH2:71][O:72]2)[CH2:67]1)=[O:87]

Participants

6

Reactant 5

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 59264488(S)-2-(Methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid2×HCID 59610664(S)-benzyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-4-oxopyrrolidine-2-carboxylateHCID 86648889HCID 86648889, compoundHCID 86708768HCID 86708768, compound

Product 1

HCID 86708767HCID 86708767, 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 (S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid and methyl (R)-2-((S)-8-(6-(9,9-difluoro-7-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-2-oxo-1-phenylethylcarbamate as 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 972.29 [M+H]+. (27.6 mg, 53%).

Sources & evidence

ORD record
ord-94f7f56a3a22461fa97e9dac2a920ec5
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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