HCID 29976790, compound → HCID 29976790, compound

HRID 1256878Notes

Reaction equation

HRID 1256878 reaction equation
Cl.[CH2:2]([N:4]([CH2:40][CH3:41])[C:5](=[O:39])[CH:6]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[O:32])=[CH:26][CH:25]=1)[C:7]([NH:9][S:10]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)(=[O:12])=[O:11])=[O:8])[CH3:3].[CH3:42][CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]2[C@:51]3([CH3:62])[C@@H:56]([CH2:57][CH2:58][C:47]=2[CH:46]=1)[C@@:55]([CH2:60][NH2:61])([CH3:59])[CH2:54][CH2:53][CH2:52]3>CO>[CH3:42][CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]2[C@:51]3([CH3:62])[C@@H:56]([CH2:57][CH2:58][C:47]=2[CH:46]=1)[C@@:55]([CH2:60][NH2:61])([CH3:59])[CH2:54][CH2:53][CH2:52]3.[CH2:40]([N:4]([CH2:2][CH3:3])[C:5](=[O:39])[C@H:6]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[O:32])=[CH:26][CH:25]=1)[C:7]([NH:9][S:10]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)(=[O:11])=[O:12])=[O:8])[CH3:41]

Participants

5

Reactant 2

HCID 29976790HCID 29976790, compoundHCID 68511991HCID 68511991, compound

Product 2

HCID 25155683HCID 25155683, compoundHCID 29976790HCID 29976790, compoundYield 140.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Resolution in the same manner as in Example 91 and using a free form of the compound (18.2 g) obtained in Example 60, (+)-dehydroabiethylamine (12.1 g) and methanol gave a (+)-dehydroabiethylamine salt (12.3 g) (optical purity>98% d.e.) of the title compound as white crystals. The salt was desalted with 2 equivalent amounts of hydrochloric acid in the same manner as in Example 91 to give the title compound (4.81 g) as a white solid (optical purity>98% e.e.).

Sources & evidence

ORD record
ord-4d5dc2ec4a044330844a59420ff52589
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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