4-Formylbenzoic acid → HCID 86678355, compound

HRID 882594Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][NH:9][C@H:10]([C:14]([NH:16][C@H:17]([C:21]([N:23]([C@@H:25]([C@@H:62]([CH3:65])[CH2:63][CH3:64])[C@H:26]([O:60][CH3:61])[CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C@H:35]([O:58][CH3:59])[C@@H:36]([CH3:57])[C:37]([NH:39][C@@:40]1([C:49]([N:51]2[CH2:56][CH2:55][CH2:54][CH2:53][O:52]2)=[O:50])[CH2:42][C@@H:41]1[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:38])=[O:29])[CH3:24])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH:11]([CH3:13])[CH3:12].[CH:66]([C:68]1[CH:76]=[CH:75][C:71]([C:72]([OH:74])=[O:73])=[CH:70][CH:69]=1)=O>>[C:72]([C:71]1[CH:75]=[CH:76][C:68]([CH2:66][N:9]([CH3:8])[C@H:10]([C:14]([NH:16][C@H:17]([C:21]([N:23]([C@@H:25]([C@@H:62]([CH3:65])[CH2:63][CH3:64])[C@H:26]([O:60][CH3:61])[CH2:27][C:28]([N:30]2[CH2:34][CH2:33][CH2:32][C@H:31]2[C@H:35]([O:58][CH3:59])[C@@H:36]([CH3:57])[C:37]([NH:39][C@@:40]2([C:49]([N:51]3[CH2:56][CH2:55][CH2:54][CH2:53][O:52]3)=[O:50])[CH2:42][C@@H:41]2[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[O:38])=[O:29])[CH3:24])=[O:22])[CH:18]([CH3:19])[CH3:20])=[O:15])[CH:11]([CH3:12])[CH3:13])=[CH:69][CH:70]=1)([OH:74])=[O:73]

Participants

Reactant 2

HCID 120884-Formylbenzoic acid

HCID 86678352HCID 86678352, compound2×

Product 1

HCID 86678355HCID 86678355, compound

Procedure

The title compound was prepared in analogy to the synthesis of Intermediate 61, by reaction of 15 mg of N-methyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino}-3-oxopropyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide trifluoroacetate (Intermediate 16) with 4-formylbenzoic acid.

Sources & evidence

ORD record: ord-03d73d77410e4144b5f05e1955a5d316
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08992932B2

Reaction notes

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