HCID 9893580, compound → HCID 86756296, compound

HRID 567436Notes

Reaction equation

HRID 567436 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C@H:10]([N:24]([CH3:36])[C:25](=[O:35])[C:26]#[C:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=3)[CH2:9][CH2:8][C@@:7]4([OH:37])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:3][CH2:2]1.[CH:38]1(CN2CC[C@]34C5C6O[C@H]3[C@@H](N(C)C(=O)CC3C=CC([Cl:70])=C(Cl)C=3)CC[C@@]4(O)[C@H]2CC=5C=CC=6O)CC1>>[ClH:70].[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C@H:10]([N:24]([CH3:36])[C:25](=[O:35])[C:26]#[C:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=3)[CH2:9][CH2:8][C@@:7]4([OH:37])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[O:20][CH3:38])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 9893580HCID 9893580, compoundHCID 15923472HCID 15923472, compound

Product 1

HCID 86756296HCID 86756296, compoundYield 76%

Procedure

The procedure of Example 132 was repeated, except that 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6β-[N-methyl-trans-3-(3-furan)acrylamido]morphinan (free base of 78) and 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6β-[N-methyl-3-(3-methylphenyl)propiolamido]morphinan (free base of 172) were used instead of 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6α-(N-methyl-3,4-dichlorophenylacetamido)morphinan (free base of 1), thereby preparing 17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxy-3-methoxy-6β-[N-methyl-trans-3-(3-furan)acrylamido]morphinan hydrochloride 217 (yield: 49%) and 17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxy-3-methoxy-6β-[N-methyl-3-(3-methylphenyl)propiolamido]morphinan hydrochloride 218 (yield: 76%).

Sources & evidence

ORD record
ord-ad9c12592f6b4bb68e036b07e0199b29
Source dataset
uspto-grants-2001_01
Patent number
US06177438B1

Reaction notes

Loading…