2,3-Dihydroxybutanedioate → HCID 86757269, compound

HRID 651052Notes

Reaction equation

[C:1]([CH:4](C(C([O-])=O)O)O)([O-])=[O:2].[CH:11]1([CH2:14][N:15]2[CH2:33][CH2:32][C@:22]34[C:23]5[C:24]6[O:31][C@H:21]3[C@H:20]([N:34]([CH3:45])[C:35](=[O:44])[CH:36]=[CH:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:19][CH2:18][C@@:17]4([OH:46])[C@H:16]2[CH2:29][C:28]=5[CH:27]=[CH:26][C:25]=6[OH:30])[CH2:13][CH2:12]1>>[CH:11]1([CH2:14][N:15]2[CH2:33][CH2:32][C@:22]34[C:23]5[C:24]6[O:31][C@H:21]3[C@H:20]([N:34]([CH3:45])[C:35](=[O:44])[CH:36]=[CH:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:19][CH2:18][C@@:17]4([O:46][C:1](=[O:2])[CH3:4])[C@H:16]2[CH2:29][C:28]=5[CH:27]=[CH:26][C:25]=6[OH:30])[CH2:12][CH2:13]1

Participants

Reactant 2

HCID 38061142,3-Dihydroxybutanedioate

HCID 69979112HCID 69979112, compound

Product 1

HCID 86757269HCID 86757269, compound

Procedure

tartrate 144 (yield: 48%) was obtained by following the procedure of example 133 but using 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-methylcinnamamido)morphinan (free base of 99) instead of 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6α-(N-methyl-3,4-dichlorophenylacetamido) morphinan (free base of 1).

Sources & evidence

ORD record: ord-b4961fdd787345b9819781ca920773cf
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277859B1

Reaction notes

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