Hydrochloric Acid → HCID 69335836, compound

HRID 844890

Reaction equation

HRID 844890 reaction equation
[C:1]([O:4][CH:5]([O:7][C:8](=[O:36])[C@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:26](=[O:35])[N:27]([CH3:34])[C:28](=[O:33])[N:29]([CH3:32])[C:30]=2[CH3:31])=[CH:21][CH:20]=1)[NH:10]C(OC(C)(C)C)=O)[CH3:6])(=[O:3])[CH3:2].[ClH:37].O1CCOCC1>C(OCC)C.ClCCl>[ClH:37].[C:1]([O:4][CH:5]([O:7][C:8](=[O:36])[C@H:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[C:26](=[O:35])[N:27]([CH3:34])[C:28](=[O:33])[N:29]([CH3:32])[C:30]=2[CH3:31])=[CH:23][CH:24]=1)[NH2:10])[CH3:6])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69337137N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester

Product 1

HCID 69335836HCID 69335836, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The solid N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester (1.4 mmol, 0.705 g) was treated with 4N hydrochloric acid in dioxane (20 mmol, 5 mL) at room temperature and the solution was stirred for 2 h as a white precipitate was formed. The mixture was diluted with diethyl ether and dichloromethane and the solids were collected by filtration washing with diethyl ether. After air drying, 0.63 g (99% yield) of 4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester hydrochloride was obtained as an amorphous gray solid. ES-HRMS m/e calcd for C20H26N3O6 (M+H) 404.1816, found 404.1818.

Workup

  1. customwas formed
  2. filtrationthe solids were collected by filtration
  3. washwashing with diethyl ether
  4. customAfter air drying

Sources & evidence

ORD record
ord-57a5a41a5c244adeb865dee7d183ec5c
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Linked notes

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