HCID 22462795, compound → HCID 22462732, compound

HRID 1937167Notes

Reaction equation

HRID 1937167 reaction equation
C(O[N:9]1[C:13](=C=O)[CH:12]([CH2:16][OH:17])[NH:11][C:10]1=[O:18])C1C=CC=CC=1.[C:19]([OH:24])(=[O:23])[C:20]([OH:22])=[O:21].[OH:25][C:26]1[CH:27]=[CH:28][C:29]2[C:33]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([CH2:41][N:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[C:37]([CH3:47])[CH:36]=3)=[C:32]([C:48]3[CH:53]=[CH:52][C:51](OCC4COC(=O)N4)=[CH:50][CH:49]=3)[S:31][C:30]=2[CH:62]=1>C1COCC1>[C:19]([OH:24])(=[O:23])[C:20]([OH:22])=[O:21].[OH:25][C:26]1[CH:27]=[CH:28][C:29]2[C:33]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([CH2:41][N:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[C:37]([CH3:47])[CH:36]=3)=[C:32]([C:48]3[CH:53]=[CH:52][C:51]([O:17][CH2:16][CH:12]4[CH2:13][NH:9][C:10](=[O:18])[NH:11]4)=[CH:50][CH:49]=3)[S:31][C:30]=2[CH:62]=1

Participants

4

Reactant 2

HCID 22462795HCID 22462795, compoundHCID 86758091HCID 86758091, compound

Product 1

HCID 22462732HCID 22462732, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By essentially following the conditions of Example 2, Part A, the title compound was prepared from 1-benzyloxy-carbonyl-2-oxo-4-hydroxymethylimidazolidine (Saijo et al. Chem. Pharm. Bull. 1980, 28, 1459) and 6-benzyloxy-3-[3-methyl-4-[(1-pyrrolidinyl)methyl]benzyl]-2-(4-hydroxyphenyl)benzo[b]thiophene (Example 8, Part C) in 28% yield following radial chromatography (SiO2; 20% then 25% then 40% THF with 5% TEA in hexanes).

Sources & evidence

ORD record
ord-b0ca64cb37874ec29c3c29da8b28e5f7
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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