Yield:-

Reaction Conditions:

with dicyclohexyl-carbodiimide in N,N-dimethyl-formamide at 50;

Steps:

1; 18.b Preparation of compound 82:
Preparation of compound 82: To a solution of desthiobiotin (214 mg, 1 mmol) in DMF (4 mL) was added DCC (227 mg, 1.1 mmol) and NHS (127 mg, 1.1 mmol). The reaction was heated to 50 °C overnight. The reaction was then cooled in an ice-bath. The solid was filtered and the filtrate was concentrated. The crude compound 82 (173 mg, 56%) was a white solid. Analytical TLC (silica gel 60), 10% MeOH in CH₂C1₂? R/ = 0.53; NMR (400 MHz, CD₃OD) δ 3.83 (quintet, / = 5.1 Hz, 1H), 3.71 (q, / = 6.9 Hz, 1H), 2.84 (s, 4H), 2.65 (t, / = 7.2 Hz, 2H), 1.75 (quintet, / = 6.9 Hz, 2H), 1.54-1.47 (m, 5H), 1.34-1.31 (m, 1H), 1.11 (d, / = 6.4 Hz, 1H); ¹³ C NMR (100 MHz, CDC1₃) δ 172.0, 170.3, 166.2, 57.3, 52.7, 31.5, 30.6, 29.7, 26.9, 26.5, 25.6, 15.6; LRMS (EI) m/z 311.2 (M⁺), 197.1; HRMS (EI) calcd for C₁₄H₂₂O₅N₃ (M⁺) m/z 311.1476, found 311.1476.

References:

VERSITECH LIMITED;MORNINGSIDE VENTURES LIMITED;YANG, Dan;GAO, Qiang;XUE, Ji-Jun;DENG, Zhangshuang;LEE, On Yi WO2016/181312, 2016, A1 Location in patent:Paragraph 0328-0331

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