1,4-Dioxane hydrochloride → HCID 56635572, compound

HRID 1980289Notes

Reaction equation

HRID 1980289 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]([O:15]C(C)(C)C)=[O:14])[N:10]([C:20](=[O:40])[C@@H:21]([NH:23][C@H:24]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:22])[C:9]1=[O:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>>[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]([OH:15])=[O:14])[N:10]([C:20](=[O:40])[C@@H:21]([NH:23][C@H:24]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:22])[C:9]1=[O:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 56605544HCID 56605544, compound

Product 1

HCID 56635572HCID 56635572, compoundYield 92.5%

Procedure

1.2 g of tert.-butyl (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-4-methyl-n-pentyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate and 30 ml of a 13% hydrogen chloride-dioxane solution are treated in the same manner as described in Example 10-(3), whereby 1.0 g of (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-4-methyl-n-pentyl)amino]-propionyl}-2-oxo-imidazolidine-4-carboxylic acid is obtained as colorless viscous oil. This oil (1.0 g) and 50 mg of palladium black are treated in the same manner as described in Example 10-(5), whereby 0.75 g of (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-carboxy-4-methyl-n-pentyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid is obtained as colorless crystals. Yield: 84.3%

Sources & evidence

ORD record
ord-e6c613a81dbc4dc9b4ec71bd5b5c235e
Source dataset
uspto-grants-1985_04
Patent number
US04508727

Reaction notes

Loading…