N-(tert-butoxycarbonyl)glycine → Glycyl-3-cyclohexyl-D-alanine

N-(tert-butoxycarbonyl)glycine (2.0 g, 11.4 mmol) and DIPEA (4.0 g, 31 mmol) were dissolved in methylene chloride (25 ml). TBTU (4.1 g, 12.8 mmol) was added and the mixture was stirred for 15 min at room temperature. 3-cyclohexyl-D-alanine (2.1 g, 12.2 mmol) was added and the reaction mixture was stirred over night at room temperature. The reaction mixture was transferred to a separation funnel and was then extracted with a water/acetic acid solution (100 ml 5% acetic acid). The organic layer was separated and evaporated under reduced pressure. The residue was dissolved in formic acid (20 ml) and the mixture was stirred over night at 40° C. The formic acid was removed under reduced pressure. The residue was washed with water (50 ml) and then stirred in aceton (25 ml) for 1 h at room temperature. The solid material was filtered off and washed with aceton (20 ml). The title compound was obtained.

1. stirringthe reaction mixture was stirred over night at room temperature
2. customThe reaction mixture was transferred to a separation funnel
3. extractionwas then extracted with a water/acetic acid solution (100 ml 5% acetic acid)
4. customThe organic layer was separated
5. customevaporated under reduced pressure
6. dissolutionThe residue was dissolved in formic acid (20 ml)
7. stirringthe mixture was stirred over night at 40° C
8. customThe formic acid was removed under reduced pressure
9. washThe residue was washed with water (50 ml)
10. stirringstirred in aceton (25 ml) for 1 h at room temperature
11. filtrationThe solid material was filtered off
12. washwashed with aceton (20 ml)

ORD record

ord-855fe6d5aaaa4061bc1a877b948d35b6

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906502B2