1,4-Dioxane hydrochloride → HCID 56618154, compound

HRID 1980290Notes

Reaction equation

HRID 1980290 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:42])[C@@H:21]([NH:23][C@H:24]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:22])[C:9]1=[O:43])[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:42])[C@@H:21]([NH:23][C@H:24]([C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33])[CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH3:22])[C:9]1=[O:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86740009HCID 86740009, compound

Product 1

HCID 56618154HCID 56618154, compoundYield 86.6%

Procedure

0.6 g of tert.-butyl (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-2-phenylethyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate and 20 ml of a 20% hydrogen chloride-dioxane solution are treated in the same manner as described in Example 10-(3), whereby 0.47 g of (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-2-phenylethyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid is obtained as colorless viscous oil. This oil (0.47 g) and 30 mg of palladium black are treated in the same manner as described in Example 10-(5), whereby 0.32 g of (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-carboxy-2-phenylethyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid is obtained as colorless crystals. Yield: 71.1%

Sources & evidence

ORD record
ord-68113391affe4bf99ba99b718c510b44
Source dataset
uspto-grants-1985_04
Patent number
US04508727

Reaction notes

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