Triethylamine → 3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-[(6-p-tolyl-pyridine-2-carbonyl)-amino]-propionic acid

HRID 405019ノート

反応式

HRID 405019 の反応式
C([O:3][C:4](=[O:49])[CH:5]([NH:33][C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)[N:37]=1)=[O:35])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[C:9]([F:32])[CH:8]=1)C.C1(C)C=CC(C2N=C(C(O)=O)C=CC=2)=CC=1.C(OC(=O)C(N)CC1C=CC(C2N=C(C3C=CC(NC(OC(C)(C)C)=O)=CC=3)ON=2)=C(F)C=1)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.C([O-])(O)=O.[Na+]>ClCCl>[C:28]([O:27][C:25]([NH:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]2[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([NH:33][C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([C:42]5[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=5)[N:37]=4)=[O:35])[C:4]([OH:49])=[O:3])=[CH:8][C:9]=3[F:32])[N:17]=2)=[CH:23][CH:22]=1)=[O:26])([CH3:31])([CH3:30])[CH3:29]

参加物

8

反応物 6

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 127849986-(4-Methylphenyl)pyridine-2-carboxylic acidHCID 66630730Ethyl 2-amino-3-(4-(5-(4-((tert-butoxycarbonyl)amino)phenyl)-1,2,4-oxadiazol-3-yl)-3-fluorophenyl)propanoateHCID 666313083-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluorophenyl}-2-[(6-p-tolyl-pyridine-2-carbonyl)-amino]-propionic acid ethyl ester

生成物 1

HCID 533718963-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-[(6-p-tolyl-pyridine-2-carbonyl)-amino]-propionic acid収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluorophenyl}-2-[(6-p-tolyl-pyridine-2-carbonyl)-amino]-propionic acid ethyl ester. A mixture of 6-p-tolyl-pyridine-2-carboxylic acid (47 mg, 0.1 mmol), 2-amino-3-{4-[5-(4-tert-butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluorophenyl}propionic acid ethyl ester (30 mg), HATU (46 mg, 0.12 mmol), and Et3N (15 mg, 0.15 mmol) in dichloromethane (5 mL) was stirred at room temperature overnight. TLC showed the reaction was completed. Saturated aqueous NaHCO3 (20 mL) was added to the mixture, and organic and aqueous layers were separated. The aqueous portion was extracted with dichloromethane (2×50 mL). The combined organic layers were washed sequentially with aq. HCl (1N, 2×50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated to give the title compound (53 mg, 80% yield).

後処理

  1. customorganic and aqueous layers were separated
  2. extractionThe aqueous portion was extracted with dichloromethane (2×50 mL)
  3. washThe combined organic layers were washed sequentially with aq. HCl (1N, 2×50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-24e28333b32043bcb2ec2a8d72d94ada
出典データセット
uspto-grants-2014_06
特許番号
US08748412B2

反応ノート

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