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

HRID 1482904ノート

反応式

HRID 1482904 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f3bdffebc9aa408cb979d46806fc47eb
出典データセット
uspto-grants-2016_08
特許番号
US09416127B2

反応ノート

読み込み中…