(E)-3-(Furan-3-yl)acryloyl chloride → 17-Cyclopropylmethyl-4,5alpha-epoxy-14beta-hydroxy-3-methoxy-6beta-[trans-3-(3-furyl)acryloylthio]morphinan

HRID 567434Notes

Reaction equation

HRID 567434 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:24][CH2:23][C@:12]34[C:13]5[C:14]6[O:22][C@H:11]3[C@H:10]([SH:25])[CH2:9][CH2:8][C@@:7]4([OH:26])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[O:20][CH3:21])[CH2:3][CH2:2]1.[O:27]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34](Cl)=[O:35])=[CH:28]1>>[CH:1]1([CH2:4][N:5]2[CH2:24][CH2:23][C@:12]34[C:13]5[C:14]6[O:22][C@H:11]3[C@H:10]([S:25][C:34](=[O:35])/[CH:33]=[CH:32]/[C:29]3[CH:30]=[CH:31][O:27][CH:28]=3)[CH2:9][CH2:8][C@@:7]4([OH:26])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[O:20][CH3:21])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 22736687(E)-3-(Furan-3-yl)acryloyl chlorideHCID 8675629117-Cyclopropylmethyl-4,5alpha-epoxy-14beta-hydroxy-3-methoxy-6beta-mercaptomorphinan

Product 1

HCID 8675629017-Cyclopropylmethyl-4,5alpha-epoxy-14beta-hydroxy-3-methoxy-6beta-[trans-3-(3-furyl)acryloylthio]morphinanYield 59%

Procedure

The procedure of Example 11 was repeated, except that 17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxy-3-methoxy-6β-mercaptomorphinan(K. Kanematsu, T. Toshiyasu, M. Yoshida., Chem., Pharm. Bull., 38, 1141, (1990)) was used instead of 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6α-(N-methylamino)morphinan 4 and trans-3-(3-furyl)acryloyl chloride was used instead of 3,4-dichlorophenylacetyl chloride, thereby preparing 17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxy-3-methoxy-6β-[trans-3-(3-furyl)acryloylthio]morphinan 169 (yield: 59%).

Sources & evidence

ORD record
ord-92a4a945d8f5416e825606f781070c2e
Source dataset
uspto-grants-2001_01
Patent number
US06177438B1

Reaction notes

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