Triethylamine → HCID 87425656, 화합물

HRID 1394130노트

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HRID 1394130 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:20][CH2:19][S:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:20][CH2:19][S:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67506663HCID 67506663, 화합물

생성물 1

HCID 87425656HCID 87425656, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of Example 17A (19.9 g, 66 mmol) and triethylamine (9.5 mL, 70 mmol) in THF (200 mL) at 0° C. under nitrogen was added methanesulfonyl chloride (15.08 g, 132 mmol) drop wise over 30 minutes. The mixture was allowed to warm up to room temperature, stirred for 12 hours, and then concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate and the aqueous layer was extracted with ethyl acetate (3×300 mL). The combined organic layers were dried (magnesium sulfate), filtered and concentrated to a yellow oil. The yellow oil was purified using a Biotage 65+ eluting with 100% ethyl acetate to provide the titled compound. MS (ESI) m/e 380 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 1.44 (m, 9H) 2.22 (m, 1H) 2.65 (m, 1H) 3.05 (m, 1H) 3.14 (d, 3H) 3.17 (m, 1H) 3.74 (m, 3.73 Hz, 1H) 3.81 (m, 2H) 4.00 (m, 1H) 4.53 (m, 1H) 4.70 (m, 2H) 5.32 (m, 1H).

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×300 mL)
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow oil
  7. customThe yellow oil was purified
  8. wash65+ eluting with 100% ethyl acetate

출처 및 근거

ORD 기록
ord-823e38b8e36848c2b666893888131e83
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348346B2

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