Hydrochloric Acid → HCID 69336846, compound

HRID 844861Notes

Reaction equation

HRID 844861 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:32])[N:22]([CH2:30][CH3:31])[C:23](=[O:29])[N:24]([CH2:27][CH3:28])[C:25]=2[CH3:26])=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.[ClH:34]>O1CCOCC1>[ClH:34].[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:32])[N:22]([CH2:30][CH3:31])[C:23](=[O:29])[N:24]([CH2:27][CH3:28])[C:25]=2[CH3:26])=[CH:18][CH:19]=1)[NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69336697HCID 69336697, compound

Product 1

HCID 69336846HCID 69336846, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3-diethyl-6-methyl-2,4-dioxo-5-pyrirnidinyl)-L-phenylalanine methyl ester (3.87 mmol, 1.78 g) in dioxane (10 mL) was added 4N hydrochloric acid in dioxane (20 mmol, 5 mL) at room temperature and the solution was stirred for 1 h. The solution was concentrated and was diluted with diethyl ether to form a white solid. The mother liquor was decanted and the residue was dried on a rotary evaporator and then under high vacuum to afford 0.72 g (47% yield) of 4-(1,3-diethyl-6-methyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester hydrochloride salt as an amorphous solid. ES-HRMS m/e calcd for C19H25N3O4 (M+Na) 382.1737, found 382.1736.

Workup

  1. concentrationThe solution was concentrated
  2. additionwas diluted with diethyl ether
  3. customto form a white solid
  4. customThe mother liquor was decanted
  5. customthe residue was dried on a rotary evaporator

Sources & evidence

ORD record
ord-c05fdfe4a3ae46a8873a3c3c18bdb473
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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