4-Methylmorpholine → (S)-tert-Butyl 2-(4-(2-phenyl-2H-1,2,3-triazole-4-carboxamido)phenyl)morpholine-4-carboxylate

HRID 1482904노트

반응식

HRID 1482904 반응식
[C:1]1([N:7]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]2[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]2)=[CH:18][CH:17]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CCOCC.O.CN(C=O)C>[C:1]1([N:7]2[N:11]=[C:10]([C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C@@H:22]4[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]4)=[CH:18][CH:17]=3)=[O:14])[CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

8

반응물 4

HCID 79724-MethylmorpholineHCID 7622772-phenyl-2H-1,2,3-triazole-4-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66705988(S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate

생성물 1

HCID 90048137(S)-tert-Butyl 2-(4-(2-phenyl-2H-1,2,3-triazole-4-carboxamido)phenyl)morpholine-4-carboxylate수율 27.1%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

In a 25 mL round-bottomed flask, 2-phenyl-2H-1,2,3-triazole-4-carboxylic acid (CAS 13306-99-5) (59.8 mg, 316 μmol, Eq: 1.1), (S)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (80 mg, 287 μmol, Eq: 1.00), N-methylmorpholine (87.2 mg, 94.8 μl, 862 μmol, Eq: 3) and HBTU (164 mg, 431 μmol, Eq: 1.5) were combined with DMF (2 ml) to give a yellow solution. The reaction mixture was stirred overnight at 60° C. The mixture was poured into water (10 ml) and extracted twice with EtOAc. The organic layers were washed with NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo to give a brown crude mixture. This mixture was diluted with ether, stirred for 15 minutes and the suspension was filtered. The resulting solid was washed several times with ether to afford the desired compound as a light-yellow solid (35 mg, 27.1%).

후처리

  1. customto give a yellow solution
  2. extractionextracted twice with EtOAc
  3. washThe organic layers were washed with NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a brown crude mixture
  8. stirringstirred for 15 minutes
  9. filtrationthe suspension was filtered
  10. washThe resulting solid was washed several times with ether

출처 및 근거

ORD 기록
ord-f3bdffebc9aa408cb979d46806fc47eb
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416127B2

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