Triethylamine → HCID 178455996、化合物

HRID 1655726ノート

反応式

HRID 1655726 の反応式
[CH2:1]([CH:8]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=O)[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][C@@H:23]([CH2:44][C:45]1[N:46]=[CH:47][NH:48][CH:49]=1)[C:24]([NH:26][C@@H:27]([CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[C@@H:28]([OH:36])[CH2:29][C@@H:30]([CH:33]([CH3:35])[CH3:34])[CH:31]=[CH2:32])=[O:25].C(N(CC)CC)C.CN(C([O:64]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:13][C:12]([CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([NH:22][C@@H:23]([CH2:44][C:45]2[N:46]=[CH:47][NH:48][CH:49]=2)[C:24]([NH:26][C@@H:27]([CH2:37][CH:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)[C@@H:28]([OH:36])[CH2:29][C@@H:30]([CH:33]([CH3:34])[CH3:35])[CH:31]=[CH2:32])=[O:25])=[O:11])=[O:64])=[CH:16][CH:17]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 193786602-(RS)-benzyl-4-(4-chlorophenyl)-4-oxo-butyric acidHCID 178456019HCID 178456019、化合物

生成物 1

HCID 178455996HCID 178455996、化合物収率 78.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.17 g (0.56 mmol) of 2-(RS)-benzyl-4-(4-chlorophenyl)-4-oxo-butyric acid was dissolved in 10 ml of dimethylformamide and treated with 0.20 g (0.51 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide, 0.057 g (0.56 mmol) of triethylamine and 0.21 g (0.56 mmol) of HBTU and stirred at room temperature overnight. The mixture was subsequently evaporated in a high vacuum. The residue was dissolved in ethyl acetate and then washed with saturated sodium bicarbonate solution and saturated sodium chloride solution. After drying the organic phase over sodium sulfate, the solvent was evaporated under reduced pressure and the residue, for purification, was chromatographed on silica gel using a 95:5 mixture of methylene chloride and methanol which contained 0.5% ammonium hydroxide. There were obtained 270 mg (78%) of (S)-α-[(RS)-α-(4-chlorophenylacetyl)hydrocinnamamido]-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide in the form of a yellowish foam. MS: 675 (M+).

後処理

  1. customThe mixture was subsequently evaporated in a high vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialAfter drying the organic phase over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue, for purification
  7. customwas chromatographed on silica gel using
  8. additiona 95:5 mixture of methylene chloride and methanol which

出典と根拠

ORDレコード
ord-02bfd85972f746b881e3b90f28bbbdbe
出典データセット
uspto-grants-1993_10
特許番号
US05250517

反応ノート

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