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

関与物質

役割	名称	HCID	仕込み量
反応物	N-(tert-butoxycarbonyl)glycine	HCID 78288	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate	HCID 6994982	—
反応物	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	(S)-Methyl 16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazahepta decane-9-carboxylate	HCID 10813484	90%

反応手順

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).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09295732B2
出典データセット	uspto-grants-2016_03
ORD ID	ord-592b604c302c49e9afa8979d89d1d26c
出典メモ	uspto-grants-2016_03