Codeine → HCID 66791479, 화합물

HRID 1096592

반응식

HRID 1096592 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH2:2]1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C@@H:24]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][C:26](O)=[O:27])=[CH:19][CH:18]=1.CN1[C@@H]2CC3C=CC(OC)=C4O[C@H]5[C@@H](O)C=C[C@@H]2[C@]5(C=34)CC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[NH:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[C@@H:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:26](=[O:27])[CH2:25][C@H:24]([NH:29][C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:23][C:20]2[CH:19]=[CH:18][C:17]([Br:16])=[CH:22][CH:21]=2)[CH2:2]1

참가 물질

7

반응물 4

HCID 5284371CodeineHCID 7009737(3R)-4-(4-bromophenyl)-3-{[(tert-butoxy)carbonyl]amino}butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 40429354HCID 40429354, 화합물

생성물 1

HCID 66791479HCID 66791479, 화합물수율 75.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

(R)-2-(Piperidin-3-yl)-1H-benzo[d]imidazole (5A) (0.29 mmol, 58 mg) in DMF (15 mL) was added (R)-4-(4-bromophenyl)-3-(tert-butoxycarbonylamino)butanoic acid (0.32 mmol, 115 mg) and N-methylmorphine (1.16 mmol, 0.13 mL). The reaction mixture was stirred at rtfor 5 min and then added HATU (0.32 mmol, 122 mg) and kept stirring at rt overnight. The reaction mixture was poured into H2O, extracted with EtOAc. The extract was washed with H2O, brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and purified by preparative LC/MS (35-60% CH3CN in H2O) to afford tert-butyl (R)-4-((R)-3-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-1-(4-bromophenyl)-4-oxobutan-2-ylcarbamate (5B) (0.22 mmol, 120 mg, two-step yield: 75.9%). ESI-MS: m/z 542.3 (M+H)+.

후처리

  1. extractionextracted with EtOAc
  2. washThe extract was washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by preparative LC/MS (35-60% CH3CN in H2O)

출처 및 근거

ORD 기록
ord-bdaf1830fb0d48f18b3b2f3d1f449c63
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138168B1

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