Sodium Chloride → HCID 59664693, compound

HRID 2422383Notes

Reaction equation

HRID 2422383 reaction equation
[CH3:1][O:2][C:3]([CH2:12][C:13]1[N:14]=[CH:15][N:16]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=1)(C(OC)=O)[C:4]([O:6][CH3:7])=[O:5].[Cl-].[Na+].C(OCC)(=O)C>CN1C(=O)CCC1.O>[CH3:1][O:2][CH:3]([CH2:12][C:13]1[N:14]=[CH:15][N:16]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 59664662HCID 59664662, compound

Product 1

HCID 59664693HCID 59664693, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of dimethyl 2-methoxy-2-((1-trityl-1H-imidazol-4-yl)methyl)malonate (0.1520 g, 0.31 mmol) and sodium chloride (0.0398 g, 0.68 mmol) in NMP (2 mL) and water (0.3 mL) was heated to 201° C. for 1 hr. After cooling to room temperature, ethyl acetate (15 mL) was added and the organic layer was washed with water (2×10 mL), saturated sodium chloride (1×10 mL) and then dried over NaSO4. Solvent removal yielded 0.1030 g of crude product. This was purified by chromatography on a silica gel 60 (11 g, 0.040 to 0.063 mm particle size) column (2.5×10 cm) using CHCl3/MeOH (98:2) as the eluent and collecting 12 mL fractions. Fractions 2 to 10 were pooled and dried, and the residue was re-purified as above, except that 5 g of silica gel was used and the eluent was CHCl3/MeOH (99:1). Fractions 10 to 16 were pooled and afforded, after drying, 0.0592 g (45%) of 94.5% pure methyl 2-methoxy-3-(1-trityl-1H-imidazol-4-yl)propanoate; retention time, 7.29 min.; column: YMC ODS-A (3 μm, 50×4.6 mm); gradient: 10% to 100% B in A over 10 min. at 1.25 mL/min. Solvent A: 0.1% TFA in water, Solvent B: 0.1% TFA in AcCN. LC/MS: ESI (M+H)+=427.1.

Workup

  1. washthe organic layer was washed with water (2×10 mL), saturated sodium chloride (1×10 mL)
  2. dry with materialdried over NaSO4
  3. customSolvent removal

Sources & evidence

ORD record
ord-a7f48abcf0cb4593bbbcf47378cbf078
Source dataset
uspto-grants-2011_06
Patent number
US07960349B2

Reaction notes

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