1,3-Thiazole-2-carbaldehyde → (S)-1-(9H-fluoren-9-yl)-14,14-dimethyl-3,12-dioxo-10-(thiazol-2-ylmethyl)-2,13-dioxa-4,10-diazapentadecane-5-carboxylic acid

참여 물질

역할	이름	HCID	투입량
반응물	1,3-Thiazole-2-carbaldehyde	HCID 2734903	—
반응물	Sodium triacetoxyborohydride	HCID 5049666	—
반응물	Tert-butyl 2-oxoacetate	HCID 10986247	—
반응물	(2S)-6-amino-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid hydrochloride	HCID 11858928	—
용매	1,2-Dichloroethane	HCID 11	—
용매	Water	HCID 962	—
생성물	(S)-1-(9H-fluoren-9-yl)-14,14-dimethyl-3,12-dioxo-10-(thiazol-2-ylmethyl)-2,13-dioxa-4,10-diazapentadecane-5-carboxylic acid	HCID 59408631	21.3%

반응 조건

온도	0 °C

반응 단계

A suspension of Fmoc-Lys-OH.HCl (6.07 g, 15 mmol) and thiazole-2-carbaldehyde (1.697 g, 15 mmol) in DCE (100 mL) was refluxed for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated sequentially with NaBH(OAc)3 (7.95 g, 37.5 mmol) and crude tert-butyl glyoxalate (3.53 g). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford (S)-1-(9H-fluoren-9-yl)-14,14-dimethyl-3,12-dioxo-10-(thiazol-2-ylmethyl)-2,13-dioxa-4,10-diazapentadecane-5-carboxylic acid (1.85 g, 21%). MS (ESI), 580 (M+H)+.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09433594B2
출처 데이터셋	uspto-grants-2016_09
ORD ID	ord-e9f775bff2744e18bab9666cd4bccb02
출처 메모	uspto-grants-2016_09