4-Oxobutanoic acid → HCID 56952594, compound

HRID 882601Notes

Reaction equation

F[C:2](F)(F)[C:3]([OH:5])=[O:4].[CH3:8][NH:9][C@H:10]([C:14]([NH:16][C@H:17]([C:21]([N:23]([C@@H:25]([C@@H:59]([CH3:62])[CH2:60][CH3:61])[C@H:26]([O:57][CH3:58])[CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C@H:35]([O:55][CH3:56])[C@@H:36]([CH3:54])[C:37]([NH:39][C@@H:40]([CH2:44][C:45]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[NH:47][CH:46]=1)[C:41]([NH2:43])=[O:42])=[O:38])=[O:29])[CH3:24])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH:11]([CH3:13])[CH3:12].O=[CH:64][CH2:65][CH2:66]C(O)=O.[C:70]([BH3-])#N.[Na+]>>[C:3]([CH2:2][CH2:64][CH2:65][CH2:66][CH2:8][N:9]([CH3:70])[C@H:10]([C:14]([NH:16][C@H:17]([C:21]([N:23]([C@@H:25]([C@@H:59]([CH3:62])[CH2:60][CH3:61])[C@H:26]([O:57][CH3:58])[CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C@H:35]([O:55][CH3:56])[C@@H:36]([CH3:54])[C:37]([NH:39][C@@H:40]([CH2:44][C:45]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[NH:47][CH:46]=1)[C:41]([NH2:43])=[O:42])=[O:38])=[O:29])[CH3:24])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH:11]([CH3:13])[CH3:12])([OH:5])=[O:4]

Participants

Reactant 3

HCID 11124-Oxobutanoic acid

HCID 5003444Sodium cyanoborohydride

HCID 71294755HCID 71294755, compound

Product 1

HCID 56952594HCID 56952594, compound

Procedure

This compound was prepared in analogy to the compound in Intermediate 82, proceeding from 20 mg (26 μmol) of N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide trifluoroacetate, by reaction with 4-oxobutanoic acid in the presence of sodium cyanoborohydride prepared.

Workup

customprepared

Sources & evidence

ORD record: ord-e1aacb4b7f444df6a2077f5484b3bf43
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08992932B2

Reaction notes

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