2,3-Dihydroxybutanedioate → HCID 131723002, compound

HRID 430709Notes

Reaction equation

HRID 430709 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]([CH3:35])[C:25](=[O:34])[CH:26]=[CH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:9][CH2:8][C@@:7]4([OH:36])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:3][CH2:2]1.Cl.C1(CN2CC[C@]34C5[C:51]6O[C@H]3[C@H](N(C)C(=O)C=CC3C=CC=CC=3)CC[C@@]4(O)[C@H]2CC=5C=C[C:52]=6[OH:57])CC1.C1(CN2CC[C@]34C5C6O[C@H]3[C@H](N(C)C(=O)C=CC3C=CC=C(C(F)(F)F)C=3)CC[C@@]4(O)[C@H]2CC=5C=CC=6O)CC1.C(C(C(C([O-])=O)O)O)([O-])=O>>[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]([CH3:35])[C:25](=[O:34])[CH:26]=[CH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:9][CH2:8][C@@:7]4([OH:36])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[O:20][C:52](=[O:57])[CH3:51])[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 38061142,3-DihydroxybutanedioateHCID 69979112HCID 69979112, compoundHCID 131723003HCID 131723003, compoundHCID 131723004HCID 131723004, compound

Product 1

HCID 131723002HCID 131723002, compound

Procedure

tartrate 140 (yield: 70%) and 17-cyclopropylmethyl-3-acetoxy-14β-hydroxy-4,5α-epoxy-6β-(N-methyl-3-trifluoromethylcinnamamido)morphinan.tartrate 141 (yield: 56%) were obtained by following the procedure of example 129 but using 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-methylcinnamamido)morphinan.tartrate 99 and 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-methyl-3-trifluoromethylcinnamamido)morphinan.tartrate 60 instead of 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6α-(N-methyl-3,4-dichlorophenylacetamido)morphinan.hydrochloride 1.

Sources & evidence

ORD record
ord-150fb4f8363e4c81b5230718e858bf1d
Source dataset
uspto-grants-2001_11
Patent number
US06323212B1

Reaction notes

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