TERT-BUTOXYCARBONYLAMINO-ACETIC ACID ETHYL ESTER

1.Ethyl 2-[(tert-butoxy)carbonylamino]acetate (5) A solution of di-tert-butyl dicarbonate (5.14 g, 23.5 mmol) in dioxane (7 mL) was added dropwise to a stirred solution of glycine ethyl ester hydrochloride 4 (3.02 g, 21.6 mmol) in water (60 mL) at 0 °C. After being left to stir for a further 15 min at this temperature, the reaction was allowed to warm slowly to rt whilst the pH was maintained at 10.5 by the addition of 2 M(aq) NaOH. After 2 h, the reaction mixture was concentrated in vacuo and the residual paste was dissolved in CH12 g glycine ester (1 eq.) was dissolved in THF (100 ml) and cooled to below 0° C. To this solution, 24.2 ml triethylamine (1.5 eq.) and 38.11 g Boc anhydride (1.5 eq.) through an additional funnel were added sequentially. Progress of the reaction was monitored by TLC using 50percent EtOAc/hexane; Rf: 0.4. Reaction mass was quenched with water and EtOAc (100 ml) was added, after 16 h. Organic layer was separated, aqueous layer was washed with EtOAc (2×40 ml) and combined organic layers were dried over sodium sulphate and concentrated under reduced pressure. Crude product was subjected to 60-120 silica gel (25percent EtOAc/hexane). Quantity produced, 20.8; yield, 88percent.12 g glycine ester (1 eq.) was dissolved in THF (100 ml) and cooled to below 0° C. To this solution, 24.2 ml triethylamine (1.5 eq.) and 38.11 g Boc anhydride (1.5 eq.) through an additional funnel were added sequentially.General procedure: L-Phenylalanine methyl ester hydrochloride (5.0 g, 23.2 mmol), triethyl amine (2.47 g, 24.4 mmol) and 2 (7.24 g, 24.4 mmol) were added to dichloromethane (50 mL) and stirred at reflux temp (38-40°C) for 5h. After completion of the reaction, filtered to remove salts and the filtrate was washed with 5percent KHSO

Molecular Weight:203.24
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:203.11575802
Monoisotopic Mass:203.11575802
Topological Polar Surface Area:64.6
Heavy Atom Count:14
Complexity:207
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes