Chloroacetaldehyde → 2-[Benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester

HRID 408577

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[CH:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].[Cl:22][CH2:23][CH:24]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:24][CH2:23][Cl:22])[CH3:6])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-benzylamino-propionic acid ethyl ester (1 eq.) in dry DCM was added MgSO4 (0.75 eq.). The reaction was cooled to 0° C. then the above solution of chloroacetaldehyde in dry DCM (solution I) and acetic acid (1 eq.) were added. Sodium triacetoxyborohydride (1.5 eq.) was added portionwise. The reaction was stirred for 1 h at 0° C. The crude was carefully quenched with a saturated aqueous solution of NaHCO3. Then aqueous NaOH (2N) was added. The aqueous layer was extracted with DCM. The combined organic layers were washed with an aqueous saturated solution of NaHCO3, then dried over MgSO4 and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc 98/2 to 95/5) to afford 2-[benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester.

Workup

customThe crude was carefully quenched with a saturated aqueous solution of NaHCO3
additionThen aqueous NaOH (2N) was added
extractionThe aqueous layer was extracted with DCM
washThe combined organic layers were washed with an aqueous saturated solution of NaHCO3
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc 98/2 to 95/5)

Sources & evidence

ORD record: ord-ebec0e38facf4fb582b154836ae73339
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Linked notes

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