Triethylamine → tert-Butyl N-(oxomethylidene)glycinate

Temperature

7.5 °C

Into a 500-mL 3-necked round-bottom flask was placed tert-butyl 2-aminoacetate (135.1, 5.9 g, 44.98 mmol, 1.00 equiv). Then dichloromethane (180 mL) and ditrichloromethyl carbonate (4.43 g, 14.93 mmol, 0.33 equiv) were added at 0° C. After 30 min triethylamine (13.65 g, 134.89 mmol, 3.00 equiv) was added to the above mixture. The resulting solution was stirred for 4 h at 5-10° C. in a water/ice bath. The solids were filtered out. The filtrate was concentrated under vacuum. The resulting solution was diluted with 50 mL of ethyl ether. The solids were filtered out. The resulting mixture was concentrated under vacuum. Purification afforded 7.1 g (crude) of tert-butyl 2-isocyanatoacetate (135.2) as a yellow oil.

1. customInto a 500-mL 3-necked round-bottom flask was placed
2. filtrationThe solids were filtered out
3. concentrationThe filtrate was concentrated under vacuum
4. additionThe resulting solution was diluted with 50 mL of ethyl ether
5. filtrationThe solids were filtered out
6. concentrationThe resulting mixture was concentrated under vacuum
7. customPurification

ORD record

ord-25f5764c8a9e41d5a0952d35f9cd92a5

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969557B2