2-(Benzenesulfonyl)-3-phenyloxaziridine → Ethyl 6-(2-ethoxy-1-hydroxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate

HRID 1468742노트

반응식

HRID 1468742 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1C[O:14]CC1.[CH2:16]([O:18][C:19](=[O:37])[CH2:20][C:21]1[C:22]([CH3:36])=[N:23][C:24]2[N:25]([N:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:30]=2)[C:26]=1[I:27])[CH3:17].C1(C2ON2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C1COCC1>[CH2:16]([O:18][C:19](=[O:37])[CH:20]([C:21]1[C:22]([CH3:36])=[N:23][C:24]2[N:25]([N:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:30]=2)[C:26]=1[I:27])[OH:14])[CH3:17]

참가 물질

5

반응물 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 86624818Khmds thfHCID 86691585Ethyl 6-(2-ethoxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate

생성물 1

HCID 86691586Ethyl 6-(2-ethoxy-1-hydroxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate수율 62.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a stirred solution of 0.9M KHMDS/THF (39.1 mL, 35.2 mmol) in THF (100 mL) at −78° C. was added a THF (50 mL) solution of ethyl 6-(2-ethoxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (11.3 g, 27.1 mmol) over the course of 5 min. After 30 min, a THF (50 mL) solution of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (9.20 g, 35.2 mmol) was added to the red reaction mixture and stirring was continued for an additional 30 min at −78° C. Then, the resulting orange reaction mixture was quenched with sat. aq. NH4Cl (50 mL), diluted with EtOAc (200 mL), washed with water (100 mL), brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo to give a solid. This solid was triturated with small amount of ethyl acetate and solids were filtered, washed with hexanes and dried under high vacuum to afford ethyl 6-(2-ethoxy-1-hydroxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (7.3 g, 16.85 mmol, 62.2% yield) as light yellow solid. 1H NMR (500 MHz, CDCl3) δ 7.33 (s, 1H), 5.75 (d, J=2.1 Hz, 1H), 4.52 (qd, J=7.1, 1.2 Hz, 2H), 4.37-4.30 (m, 2H), 3.57 (d, J=2.4 Hz, 1H), 2.63 (s, 3H), 1.48 (t, J=7.2 Hz, 3H), 1.27 (t, J=7.0 Hz, 3H). LCMS (M+H)=434.1.

후처리

  1. waitwas continued for an additional 30 min at −78° C
  2. customThen, the resulting orange reaction mixture was quenched with sat. aq. NH4Cl (50 mL)
  3. additiondiluted with EtOAc (200 mL)
  4. washwashed with water (100 mL), brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a solid
  9. customThis solid was triturated with small amount of ethyl acetate and solids
  10. filtrationwere filtered
  11. washwashed with hexanes
  12. customdried under high vacuum

출처 및 근거

ORD 기록
ord-612747ae637c4734aea9a0a5f721c3c5
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006235B2

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