4-Oxobutanoic acid → HCID 71294584, compound

HRID 882604Notes

Reaction equation

[CH3:1][NH:2][C@H:3]([C:7]([NH:9][C@H:10]([C:14]([N:16]([C@@H:18]([C@@H:48]([CH3:51])[CH2:49][CH3:50])[C@H:19]([O:46][CH3:47])[CH2:20][C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C@H:28]([O:44][CH3:45])[C@@H:29]([CH3:43])[C:30]([NH:32][C@H:33]([CH3:42])[C@@H:34]([OH:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:31])=[O:22])[CH3:17])=[O:15])[CH:11]([CH3:13])[CH3:12])=[O:8])[CH:4]([CH3:6])[CH3:5].O=[CH:53][CH2:54][CH2:55][C:56]([OH:58])=[O:57].C([BH3-])#N.[Na+]>>[C:56]([CH2:55][CH2:54][CH2:53][N:2]([CH3:1])[C@H:3]([C:7]([NH:9][C@H:10]([C:14]([N:16]([C@@H:18]([C@@H:48]([CH3:51])[CH2:49][CH3:50])[C@H:19]([O:46][CH3:47])[CH2:20][C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C@H:28]([O:44][CH3:45])[C@@H:29]([CH3:43])[C:30]([NH:32][C@H:33]([CH3:42])[C@@H:34]([OH:41])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:31])=[O:22])[CH3:17])=[O:15])[CH:11]([CH3:12])[CH3:13])=[O:8])[CH:4]([CH3:6])[CH3:5])([OH:58])=[O:57]

Participants

Reactant 3

HCID 11124-Oxobutanoic acid

HCID 5003444Sodium cyanoborohydride

HCID 11542188Monomethyl auristatin E2×

Product 1

HCID 71294584HCID 71294584, compound

Procedure

100 mg (0.139 mmol) of N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide (Intermediate 40) were used, in analogy to the preparation of Intermediate 61, by reaction with 4-oxobutanoic acid in the presence of sodium cyanoborohydride, to obtain 94 mg (84% of theory) of the title compound. The title compound was purified by preparative HPLC.

Sources & evidence

ORD record: ord-6dd4e3a293e4467db72b3f42a4815580
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08992932B2

Reaction notes

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