Citric Acid → HCID 178490234、化合物

HRID 540390ノート

反応式

HRID 540390 の反応式
[CH3:1]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:32]1[CH:36]=[C:35]([CH2:37][CH2:38][C:39]([NH:41][C@H:42]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)[C:43]([OH:45])=O)=[O:40])[N:34]=[CH:33]1.[F:55][C:56]([F:61])([F:60])[C:57]([OH:59])=[O:58].[OH:62][C:63]1([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[CH2:66][NH:65][CH2:64]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.CN(C=O)C.CN(C=O)C>[F:55][C:56]([F:61])([F:60])[C:57]([OH:59])=[O:58].[OH:62][C:63]1([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=2[CH3:1])[CH2:66][N:65]([C:43](=[O:45])[C@@H:42]([NH:41][C:39](=[O:40])[CH2:38][CH2:37][C:35]2[N:34]=[CH:33][NH:32][CH:36]=2)[CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)[CH2:64]1

参加物

8

反応物 5

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 669881473-Phenylazetidin-3-ol; trifluoroacetic acidHCID 178490237HCID 178490237、化合物

生成物 1

HCID 178490234HCID 178490234、化合物収率 10%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

2 ml of DMF, 106 mg (0.33 mmol) of TBTU and 1 ml of DIEA are added to 105 mg (0.33 mmol) of (R)-2-(3-1H-imidazol-4-ylpropionylamino)-3-(4-methoxyphenyl)propanoic acid. The reaction medium is left to stir for 15 minutes at ambient temperature. 36 mg (0.13 mmol) of 3-hydroxy-3-phenylazetidine trifluoroacetate dissolved in 5 ml of a 1/4 DCM/DMF solution are added dropwise and stirred at ambient temperature for 16 hours. A 5% citric acid solution is added, followed by extraction with dichloromethane. The organic phase is washed with a saturated solution of potassium hydrogen carbonate. The organic phase is dried and evaporated to dryness. The crude product obtained is purified by silica gel chromatography (eluent 9/1 dichloromethane/methanol). 6 mg of N—[(S)-2-(3-hydroxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]-3-(1H-imidazol-4-yl)propionamide trifluoroacetate are obtained in the form of a white powder with a yield of 10%.

後処理

  1. waitThe reaction medium is left
  2. additionare added dropwise
  3. stirringstirred at ambient temperature for 16 hours
  4. extractionfollowed by extraction with dichloromethane
  5. washThe organic phase is washed with a saturated solution of potassium hydrogen carbonate
  6. customThe organic phase is dried
  7. customevaporated to dryness
  8. customThe crude product obtained
  9. customis purified by silica gel chromatography (eluent 9/1 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-6dfb1bf36ee547d9ad34776beba18edb
出典データセット
uspto-grants-2014_10
特許番号
US08871187B2

反応ノート

読み込み中…