1,2-Dichloroethane → [[2-(Methoxymethylamino)-2-oxoethyl][(phenylmethoxy)carbonyl]amino]-acetic acid

Temperature

0 °C

To a solution of N-[(benzyloxy)carbonyl]-N-(carboxymethyl)glycine (28.45 g, 106.46 mmol) in DMF (163 mL) was added EDC (24.08 g, 125.62 mmol). The solution was cooled to 0° C. and treated with a mixture of N-methoxymethylamine hydrochloride (12.25 g, 125.62 mmol) and Hunig's base (21.88 mL, 125.62 mmol) in DMF (55 mL). The reaction was stirred at room temperature overnight and poured over a mixture of ice and aqueous 10% HCl solution. The mixture was extracted twice with EtOAc. The combined organics were washed twice with aqueous 10% HCl solution and once with brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford a crude oil which was suspended in saturated aqueous NaHCO3 solution. The mixture was washed with EtOAc, adjusted to pH 2 with aqueous 1N HCl, and extracted three times with EtOAc. The final three organic extracts were combined, dried over MgSO4, filtered, and concentrated in vacuo to afford the product as a golden oil.

1. extractionThe mixture was extracted twice with EtOAc
2. washThe combined organics were washed twice with aqueous 10% HCl solution and once with brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto afford a crude oil which
7. washThe mixture was washed with EtOAc
8. extractionextracted three times with EtOAc
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-5f9615fc4fea4aae9d6082b42316b8bc

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07435735B2