Dichloromethane → D-Serine benzyl ester hydrochloride

HRID 582601Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:21])[C@@H:10]([CH2:19][OH:20])[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:30]>>[ClH:30].[CH2:1]([O:8][C:9](=[O:21])[C@@H:10]([CH2:19][OH:20])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 12953536Benzyl N-(tert-butoxycarbonyl)-D-serinate

Product 1

HCID 11776084D-Serine benzyl ester hydrochloride

Procedure

A solution of Boc-(D)-serine benzyl ester (1.1 g) in 1/1 mixture of the TFA and methylene chloride was stirred for 1 hour and then concentrated and azeotroped from toluene to give D-serine benzyl ester HCl salt. The residue was dissolved in methylene (15 ml), and added methyl benzimidate HCl (732 mg) and TEA (0.5 ml). The mixture was stirred at room temperature for 3 hours and then concentrated. Purification by flash chromatography (hexanes/ethyl acetate=6/1) gave 572 mg of the title compounds.

Workup

concentrationconcentrated
customazeotroped from toluene

Sources & evidence

ORD record: ord-cf14e2cd62e34ee2aacef10e8e0fa71f
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05925659

Reaction notes

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