4-Oxobutanoic acid → HCID 56952799, compound

HRID 879253Notes

Reaction equation

HRID 879253 reaction equation
FC(F)(F)C([O-])=O.[Na+].[CH3:9][NH:10][C@H:11]([C:15]([NH:17][C@H:18]([C:22]([N:24]([C@@H:26]([C@@H:67]([CH3:70])[CH2:68][CH3:69])[C@H:27]([O:65][CH3:66])[CH2:28][C:29]([N:31]1[CH2:35][CH2:34][CH2:33][C@H:32]1[C@H:36]([O:63][CH3:64])[C@@H:37]([CH3:62])[C:38]([NH:40][C@@H:41]([CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[CH2:42][O:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]([O:53][CH3:54])=[O:52])=[CH:47][CH:46]=1)=[O:39])=[O:30])[CH3:25])=[O:23])[CH:19]([CH3:21])[CH3:20])=[O:16])[CH:12]([CH3:14])[CH3:13].O=[CH:72][CH2:73][CH2:74][C:75]([OH:77])=[O:76].C([BH3-])#N.[Na+].O1CCOCC1>O1CCOCC1.O>[C:75]([CH2:74][CH2:73][CH2:72][N:10]([CH3:9])[C@H:11]([C:15]([NH:17][C@H:18]([C:22]([N:24]([C@@H:26]([C@@H:67]([CH3:70])[CH2:68][CH3:69])[C@H:27]([O:65][CH3:66])[CH2:28][C:29]([N:31]1[CH2:35][CH2:34][CH2:33][C@H:32]1[C@H:36]([O:63][CH3:64])[C@@H:37]([CH3:62])[C:38]([NH:40][C@@H:41]([CH2:55][C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)[CH2:42][O:43][CH2:44][C:45]1[CH:46]=[CH:47][C:48]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][CH:50]=1)=[O:39])=[O:30])[CH3:25])=[O:23])[CH:19]([CH3:20])[CH3:21])=[O:16])[CH:12]([CH3:14])[CH3:13])([OH:77])=[O:76]

Participants

6

Reactant 4

HCID 11124-Oxobutanoic acidHCID 312751,4-DioxaneHCID 5003444Sodium cyanoborohydrideHCID 86698267HCID 86698267, compound2×

Product 1

HCID 56952799HCID 56952799, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

11.5 mg (12 μmol) of N-methyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-3-{[(2S)-1-{[4-(methoxycarbonyl)benzyl]oxy}-3-phenylpropane-2-yl]amino}-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide sodium trifluoroacetate (intermediate 46) were dissolved in 0.7 ml of dioxane/water (1:1) and treated in analogy to example 1 with 15 aqueous solution of 4-ketobutyric acid in the presence of sodium cyanoborohydride. Following lyophilization from dioxane, the yield was 8.3 mg (74% o. th.) of the title compound in the form of a white solid substance.

Sources & evidence

ORD record
ord-708889edb17c4fd0bb71e382224ff36e
Source dataset
uspto-grants-2015_03
Patent number
US08987209B2

Reaction notes

Loading…