Ethyl benzimidate → HCID 15719240, compound

HRID 988012Notes

Reaction equation

HRID 988012 reaction equation
Cl.C[O:3][C:4](=[O:9])[C@H:5](CO)N.[C:10](=[NH:20])([O:17][CH2:18][CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O.ClCCl>[C:11]1([C:10]2[O:17][CH2:18][CH:19]([CH2:5][C:4]([OH:9])=[O:3])[N:20]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 79250Ethyl benzimidateHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 15719240HCID 15719240, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

567 mg (3.6 mmol) of L-serine methyl ester hydrochloride are dissolved in 0.5 ml of water, and 610 mg (3.6 mmol) of ethyl benzimidate in 10 ml of dichloromethane are added thereto. After 48 h at reflux, the mixture is concentrated to a volume of 50 ml of dichloromethane and washed with NaHCO3 (3×10 ml), and the aqueous phase is extracted with ethyl acetate (2×10 ml). Column chromatography (15×5 cm, hexane/ethyl acetate 1:1) yields 3.0 g of A2a (91% of theory).

Workup

  1. temperatureAfter 48 h at reflux
  2. concentrationthe mixture is concentrated to a volume of 50 ml of dichloromethane
  3. washwashed with NaHCO3 (3×10 ml)
  4. extractionthe aqueous phase is extracted with ethyl acetate (2×10 ml)
  5. customColumn chromatography (15×5 cm, hexane/ethyl acetate 1:1) yields 3.0 g of A2a (91% of theory)

Sources & evidence

ORD record
ord-316f4ead516442c4a79299d8e0565805
Source dataset
uspto-grants-2003_10
Patent number
US06632954B2

Reaction notes

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