Sulfuric Acid → (-)-2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide

HRID 367350Notes

Reaction equation

HRID 367350 reaction equation
[OH:1][C@H:2]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([CH2:31][OH:32])[CH:25]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([N:19]3[CH2:23]CC[CH2:20]3)=[O:18])=[CH:10][CH:11]=2)[CH2:6]1.S(=O)(=O)(O)O.C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.C(O)(=O)[C@H]([C@@H](C(O)=O)O)O>>[OH:1][C@H:2]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([CH2:31][OH:32])[CH:25]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([N:19]([CH3:23])[CH3:20])=[O:18])=[CH:10][CH:11]=2)[CH2:6]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 439655D-Tartaric acidHCID 444305L-Tartaric acidHCID 15485660(-)-1-[2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxy-3hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetyl]pyrrolidine2×

Product 1

HCID 9811600(-)-2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide

Procedure

Using (-)-1-[2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetyl]pyrrolidine (Compound 7) and sulfuric acid, L-tartaric acid or D-tartaric acid, the following salts were obtained in the same manner as that described in Example 7.

Workup

  1. customthe following salts were obtained in the same manner as

Sources & evidence

ORD record
ord-df0d7820dedd4d0298451668fa9d5686
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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