Dimethylformamide → HCID 178455998、化合物

HRID 1655728ノート

反応式

HRID 1655728 の反応式
C(OC(=O)[CH2:5][CH:6]([CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=O)C.[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([CH2:55][CH3:56])CC)C.CN([C:60]([O:64]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C)C=[O:84]>C(#N)C>[CH2:55]([O:84][C:60](=[O:64])[CH:10]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH:6]([C:7](=[O:9])[NH:22][C@H:23]([C:24](=[O:25])[NH:26][C@@H:27]([CH2:37][CH:38]1[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1)[C@@H:28]([OH:36])[CH2:29][C@@H:30]([CH:33]([CH3:34])[CH3:35])[CH:31]=[CH2:32])[CH2:44][C:45]1[N:46]=[CH:47][NH:48][CH:49]=1)[CH3:5])[CH3:56]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 538675143-(RS)-(1-naphthylmethyl)succinic acid 1-ethyl esterHCID 178456019HCID 178456019、化合物

生成物 1

HCID 178455998HCID 178455998、化合物収率 45%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

109 mg (0.38 mmol) of 3-(RS)-(1-naphthylmethyl)succinic acid 1-ethyl ester were dissolved in 6 ml of acetonitrile and 1 ml of dimethylformamide and, after the addition of 135 mg (0.35 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide, 39 mg (0.38 mmol) of triethylamine and 144 mg (0.38 mmol) of HBTU, stirred at room temperature for 6 hours. Subsequently, the reaction solution was evaporated in a high vacuum and the residue was dissolved in 50 ml of ethyl acetate and washed 3 times with 10 ml of saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and evaporated under reduced pressure, and the residue was chromatographed on silica gel with a 95:5 mixture of methylene chloride and methanol which contained 0.1% ammonium hydroxide, to obtain 103 mg (45%) of (RS)-β-[[(S)-1-[[(1S,2S, 4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]-carbamoyl]-1-naphthylbutyric acid ethyl ester as a yellowish foam. MS: 594 (M-ethanol-water)+

後処理

  1. customSubsequently, the reaction solution was evaporated in a high vacuum
  2. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
  3. washwashed 3 times with 10 ml of saturated sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customthe residue was chromatographed on silica gel with a 95:5 mixture of methylene chloride and methanol which

出典と根拠

ORDレコード
ord-61cd95a575b2477082ebc55f7a3ab5e8
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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