1,4-Dioxane hydrochloride → HCID 57048546, compound

HRID 1980285Notes

Reaction equation

HRID 1980285 reaction equation
Cl.O1CCOCC1.[CH2:8]([N:15]1[CH2:19][C@@H:18]([C:20]([O:22]C(C)(C)C)=[O:21])[N:17]([C:27](=[O:50])[C@@H:28]([NH:30][C@H:31]([C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])[CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:29])[C:16]1=[O:51])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([N:15]1[CH2:19][C@@H:18]([C:20]([OH:22])=[O:21])[N:17]([C:27](=[O:50])[C@@H:28]([NH:30][C@H:31]([C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])[CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH3:29])[C:16]1=[O:51])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57007444HCID 57007444, compound

Product 1

HCID 57048546HCID 57048546, compoundYield 91.9%

Procedure

20 ml of a 13% hydrogen chloride-dioxane solution are added to 1.2 g of tert.-butyl (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate, and the mixture is allowed to stand at room temperature overnight. The mixture is concentrated under reduced pressure to remove solvent. Ethyl acetate and water are added to the residue and the mixture is adjusted to pH 5 to 6 with an aqueous sodium bicarbonate solution. The ethyl acetate layer is collected therefrom, washed with a saturated sodium chloride solution and dried. The resultant solution is concentrated under reduced pressure to remove solvent, whereby 1.0 g of (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid is obtained as colorless viscous oil. Yield: 91.9%

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto remove solvent
  3. additionEthyl acetate and water are added to the residue
  4. customThe ethyl acetate layer is collected
  5. washwashed with a saturated sodium chloride solution
  6. customdried
  7. concentrationThe resultant solution is concentrated under reduced pressure
  8. customto remove solvent

Sources & evidence

ORD record
ord-55f776a20da74f8c895c8ceb2a1af5e3
Source dataset
uspto-grants-1985_04
Patent number
US04508727

Reaction notes

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