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 acetone (25 ml) for 1 h at room temperature. The solid material was filtered off and washed with acetone (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 acetone (25 ml) for 1 h at room temperature
11. filtrationThe solid material was filtered off
12. washwashed with acetone (20 ml)

ORD record

ord-2a7c6f5f837042ad9bf766dcff17f663

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842684B2