4-Oxobutanoic acid → HCID 66548247, compound

HRID 573023Notes

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:53]([CH3:56])[CH2:54][CH3:55])[C@H:26]([O:51][CH3:52])[CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C@H:35]([O:49][CH3:50])[C@@H:36]([CH3:48])[C:37](=[O:47])[NH:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:29])[CH3:24])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH:11]([CH3:13])[CH3:12].O=[CH:58][CH2:59][CH2:60][C:61]([OH:63])=[O:62].C([BH3-])#N.[Na+]>>[C:61]([CH2:60][CH2:59][CH2:58][N:9]([CH3:8])[C@H:10]([C:14]([NH:16][C@H:17]([C:21]([N:23]([C@@H:25]([C@@H:53]([CH3:56])[CH2:54][CH3:55])[C@H:26]([O:51][CH3:52])[CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C@H:35]([O:49][CH3:50])[C@@H:36]([CH3:48])[C:37](=[O:47])[NH:38][CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:29])[CH3:24])=[O:22])[CH:18]([CH3:19])[CH3:20])=[O:15])[CH:11]([CH3:13])[CH3:12])([OH:63])=[O:62]

Participants

Reactant 3

HCID 11124-Oxobutanoic acid

HCID 5003444Sodium cyanoborohydride

HCID 86712515HCID 86712515, compound2×

Product 1

HCID 66548247HCID 66548247, compound

Procedure

The title compound was synthesized by analogy with the synthesis process of Example 1 by reacting 57 mg (71 μmol) N-methyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[(2-phenylethyl)amino]propyl}pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide trifluoroacetic acid salt (intermediate 25) with a 15% aqueous solution of 4-oxobutanoic acid in the presence of sodium cyanoborohydride.

Sources & evidence

ORD record: ord-0f2c94fb64b64fc6be511222d27e9047
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029406B2

Reaction notes

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