Triethylamine → HCID 66991148, 화합물

HRID 2367383

반응식

HRID 2367383 반응식
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH:16]([C:20]([OH:22])=O)[CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[NH2:30][CH2:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=1)=[O:33]>C(Cl)Cl.CN(C=O)C.O>[CH3:41][O:40][C:36]1[CH:35]=[C:34]([C:32](=[O:33])[CH2:31][NH:30][C:20]([CH:16]2[O:17][CH2:18][CH2:19][N:14]([CH2:13][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:15]2)=[O:22])[CH:39]=[CH:38][CH:37]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27763534-Benzylmorpholine-2-carboxylic acidHCID 7176074HCID 7176074, 화합물

생성물 1

HCID 66991148HCID 66991148, 화합물수율 50%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
25 °C

실험 절차

Oxalyl chloride (1.139 mL, 13.02 mmol) was added to a suspension of 4-(phenylmethyl)-2-morpholinecarboxylic acid (2.237 g, 8.68 mmol) and DMF (0.034 mL, 0.434 mmol) in CH2Cl2 (80 mL) at 0° C., and the resulting mixture was stirred at 25° C. for 2 hours. The mixture was concentrated, and the resulting residue was dissolved in CH2Cl2 (80 mL). The resulting brown solution was added to a suspension of triethylamine (3.63 mL, 26.0 mmol) and 2-amino-1-[3-(methyloxy)phenyl]ethanone (1.75 g, 8.68 mmol) in CH2Cl2 at 0° C., and the reaction mixture was stirred at 25° C. for 3 hours. Water (150 mL) was added to the reaction mixture, and the resulting mixture was extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. Purification by silica gel chromatography eluting with EtOAc in PE from 0% to 50% afforded the title compound (1.6 g) as an orange oil. LC-MS (ES) m/z=369 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated
  2. dissolutionthe resulting residue was dissolved in CH2Cl2 (80 mL)
  3. stirringthe reaction mixture was stirred at 25° C. for 3 hours
  4. extractionthe resulting mixture was extracted with CH2Cl2 (3×100 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography
  9. washeluting with EtOAc in PE from 0% to 50%

출처 및 근거

ORD 기록
ord-da14d53c022342ebb2cc08d1e9305aa2
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

연결된 노트

불러오는 중…