反応 #589714

反応方程式

di-tert-butylphosphate

2b

Acetyl-{(R)-3-[3-fluoro-4-(2-methyl-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-5-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid 1-chloro-ethyl ester

sodium iodide

→

title compound

収率 76.5%

Acetyl-{(R)-3-[3-fluoro-4-(2-methyl-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-5-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid 1-(di-tert-butoxy-phosphoryloxy)-ethyl ester

収率 76.5%

溶媒

THF

反応条件

後処理

1. 1
   濃縮concentrated in vacuo
2. 2
   workup.DISSOLUTIONdissolved in DMSO
3. 3
   ろ過filtered
4. 4
   その他purified directly by HPLC (C-18 column, 30-100% gradient elution, MeCN:H2O)
5. 5
   workup.ADDITIONFractions containing product

実験手順

To a solution of 2b (75 mg, 0.16 mmol) in THF (1.5 mL) was added sodium iodide (66 mg, 0.44 mmol) and the tetrabutylammonium salt of di-tert-butylphosphate (200 mg, 0.04 mmol). The reaction mixture was heated at 65° C. for 48 h, concentrated in vacuo, dissolved in DMSO, filtered, and purified directly by HPLC (C-18 column, 30-100% gradient elution, MeCN:H2O). Fractions containing product were lyophilized to give 20 mg (20%) of the title compound as a 1:1 mixture of diastereomers. 1H NMR (400 MHz, DMSO-d6): δ 7.53 (s, 1H), 7.44-7.39 (m, 1H), 7.17-7.14 (m, 1H), 6.90-6.85 (m, 1H), 6.45-6.38 (m, 1H), 4.85-4.75 (m, 1H), 4.48-4.46 (m, 4H), 4.25-4.08 (m, 2H), 3.95-3.77 (m, 2H), 3.85 (s, 3H), 2.47-2.48 (m, 3H), 1.56-1.54 (m, 3H), 1.41-1.40 (m, 18H). MS 654 (M+1)+

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