N-(tert-butoxycarbonyl)glycine → (S)-Methyl 16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazahepta decane-9-carboxylate

참여 물질

역할	이름	HCID	투입량
반응물	N-(tert-butoxycarbonyl)glycine	HCID 78288	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate	HCID 6994982	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
용매	Dimethylformamide	HCID 6228	—
생성물	(S)-Methyl 16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazahepta decane-9-carboxylate	HCID 10813484	90%

반응 단계

To a solution of L-Lys(Z)OMe 40 (1.05 g, 2.6 mmol) in dry DMF (40 mL) was added Boc-GlyOH (494 mg, 2.8 mmol), HATU (977 mg, 2.57 mmol), and DIEA (2.03 mL, 11.7 mmol). The mixture was stirred at rt overnight. The solvent was then removed in vacuo and the residue was dissolved in EtOAc (100 mL) and washed with saturated NaHCO3 solution water and brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude compound was purified on column of silica gel (2% MeOH/DCM) to give the subject compound (960 mg, yield 90%). Intermediate 41 was characterized by the following spectroscopic data: 1H NMR (DMSO-d6, 300 MHz) δ (ppm) 8.12 (t, 1H), 7.98 (t, 1H), 7.47-7.38 (m, 5H), 6.98 (t, 1H), 5.13 (s, 2H), 4.56 (m, 1H), 4.05 (d, 2H), 3.65 (s, 3H), 3.02 (m, 2H), 1.90 (m, 2H), 1.55 (m, 2H), 1.38 (s, 9H), 1.25 (m, 2H).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09295732B2
출처 데이터셋	uspto-grants-2016_03
ORD ID	ord-592b604c302c49e9afa8979d89d1d26c
출처 메모	uspto-grants-2016_03