Morpholine → Tert-butyl 4-(morpholinomethyl)thiazol-2-ylcarbamate

HRID 520488

반응식

HRID 520488 반응식
O[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[S:6][CH:7]=1.CCN(CC)CC.CS(Cl)(=O)=O.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>C(Cl)Cl>[O:31]1[CH2:32][CH2:33][N:28]([CH2:2][C:3]2[N:4]=[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[S:6][CH:7]=2)[CH2:29][CH2:30]1

참가 물질

6

반응물 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22280475(4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

생성물 1

HCID 58154672Tert-butyl 4-(morpholinomethyl)thiazol-2-ylcarbamate수율 72.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

tert-Butyl 4-(hydroxymethyl)thiazol-2-ylcarbamate 89 (2.00 g, 8.68 mmol) was taken up in 25 mL of CH2Cl2 along with Et3N (1.82 mL, 13.05 mmol) and cooled to 0° C. Methanesulfonyl chloride (0.85 mL, 10.88 mmol) was added and the resulting reaction mixture was stirred at 0° C. for 60 min. Morpholine 63 (3.0 mL, 35 mmol) was then added and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure. The resulting residue was taken up in EtOAc and washed with dilute aqueous NaHCO3, brine, dried with Na2SO4, and concentrated under reduced pressure. This material was purified by filtering through a short column of silica gel. The filtrate was concentrated to afford 90 (1.88 g, 69% yield).

후처리

  1. customthe resulting reaction mixture
  2. stirringthe reaction mixture was stirred at room temperature for 18 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washwashed with dilute aqueous NaHCO3, brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThis material was purified
  8. filtrationby filtering through a short column of silica gel
  9. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-ded2a1763b7646699b6e7d47fecf5e4c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326986B2

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