반응 #92795

반응 방정식

7-(Boc-leucinyl)aminonaphtho[2,1-d]thiazole-2-carbonitrile

thioanisole

D-cysteine hydrochloride hydrate

potassium carbonate

Trifluoroacetic acid

→

2-(7-(Leucinyl)aminonaphtho[2,1-d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

용매

DCM

반응 조건

후처리

1. 1
   기타solvents were removed under reduced pressure
2. 2
   기타the remaining residue triturated with ether
3. 3
   workup.WAITAfter 20 min
4. 4
   여과the reaction was filtered
5. 5
   기타the product was isolated by preparative HPLC
6. 6
   세척eluting with 2→50% MeCN in 0.1% formic acid

실험 절차

7-(Boc-leucinyl)aminonaphtho[2,1-d]thiazole-2-carbonitrile (69 mg, 0.16 mmol) was combined with 0.5 mL of thioanisole and 1.5 mL of DCM and stirred in an ice bath. Trifluoroacetic acid (1.5 mL) was added, and the reaction monitored by HPLC. After 1 h, solvents were removed under reduced pressure, and the remaining residue triturated with ether. The resulting solid was taken up in MeCN/H2O and treated with D-cysteine hydrochloride hydrate (55 mg, 0.31 mmol) and potassium carbonate (55 mg, 0.40 mmol). After 20 min, the reaction was filtered and the product was isolated by preparative HPLC eluting with 2→50% MeCN in 0.1% formic acid. Calcd for C21H23N4O3S2 (M+H): 443.1. found 443.

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