Water → N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester

HRID 844889Notes

Reaction equation

HRID 844889 reaction equation
[CH3:1][C:2]([CH3:30])([O:4][C:5]([NH:7][C@H:8]([C:27]([OH:29])=[O:28])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17](=[O:26])[N:18]([CH3:25])[C:19](=[O:24])[N:20]([CH3:23])[C:21]=2[CH3:22])=[CH:12][CH:11]=1)=[O:6])[CH3:3].C(=O)(O)[O-].[Na+].[C:36]([O:39][CH:40](Cl)[CH3:41])(=[O:38])[CH3:37].O>CN(C=O)C>[C:36]([O:39][CH:40]([O:28][C:27](=[O:29])[C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17](=[O:26])[N:18]([CH3:25])[C:19](=[O:24])[N:20]([CH3:23])[C:21]=2[CH3:22])=[CH:12][CH:11]=1)[NH:7][C:5]([O:4][C:2]([CH3:30])([CH3:1])[CH3:3])=[O:6])[CH3:41])(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 5218651-Chloroethyl acetateHCID 69337268N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine

Product 1

HCID 69337137N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine (1.006 mmol, 420 mg) and sodium bicarbonate (5.03 mmol, 422 mg) in DMF (8 mL) was added 1-chloroethyl acetate (5.03 mmol, 616 mg) at room temperature. The reaction mixture was stirred for 48 h. Then, it was poured into water (50 mL) and was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with water (2×50 mL) and brine solution (100 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the filtrate gave the crude product which was purified by silica gel chromatography using a Biotage (40s) column to obtain 390 mg (77% yield) of N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester as an amorphous white solid. ES-HRMS m/e calcd for C25H33N3O8 (M+Na) 526.2160, found 526.2143.

Workup

  1. extractionwas extracted with ethyl acetate (3×50 mL)
  2. washThe combined extracts were washed with water (2×50 mL) and brine solution (100 mL)
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. filtrationFiltration of the drying agent and concentration of the filtrate
  5. customgave the crude product which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-c3ba14a5f8064e1bba4d6ad9bd0ab408
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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