Sodium Carbonate → HCID 53706240, compound

HRID 276717Notes

Reaction equation

HRID 276717 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])[NH2:7].C([O-])([O-])=O.[Na+].[Na+].[C:20]1([CH:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O.C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])[NH:7][C:27](=[O:28])[CH:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 746372,2-Diphenylacetyl chlorideHCID 27614943-Methylphenylalanine

Product 1

HCID 53706240HCID 53706240, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methyl-L-phenylalanine (1.8 g, 10.06 mmol) and Na2CO3 (3.2 g, 3.0.18 mmol) in water (150 mL) is added a solution of diphenylacetyl chloride (2.32 g, 10.06 mmol) in THF (150 mL), and the resulting solution is stirred vigorously at room temperature overnight. The THF is then evaporated and the aqueous layer is diluted with 6% aqueous Na2CO3 (100 mL), and washed with Et2O (3×150 mL). The aqueous layer is then acidified to pH 1 with conc. HCl, and the resulting slurry is extracted with EtOAc (3×100 mL). The organic phase is then washed with water (2×100 mL) and brine (1×100 mL), dried over MgSO4 and evaporated to yield 3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanine, as a white solid.

Workup

  1. customThe THF is then evaporated
  2. additionthe aqueous layer is diluted with 6% aqueous Na2CO3 (100 mL)
  3. washwashed with Et2O (3×150 mL)
  4. extractionthe resulting slurry is extracted with EtOAc (3×100 mL)
  5. washThe organic phase is then washed with water (2×100 mL) and brine (1×100 mL)
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-60f8bb385ef446c28b2977ed12a20ca8
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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