Ethylmorpholine → HCID 178455995、化合物

HRID 1655710ノート

反応式

HRID 1655710 の反応式
[CH2:1]([CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C@@H:20]([CH2:41][C:42]1[N:43]=[CH:44][NH:45][CH:46]=1)[C:21]([NH:23][C@@H:24]([CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C@@H:25]([OH:33])[CH2:26][C@@H:27]([CH:30]([CH3:32])[CH3:31])[CH:28]=[CH2:29])=[O:22].C(N1CCOCC1)C.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O>[CH:35]1([CH2:34][C@H:24]([NH:23][C:21](=[O:22])[C@@H:20]([NH:19][C:9](=[O:11])[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:41][C:42]2[N:43]=[CH:44][NH:45][CH:46]=2)[C@@H:25]([OH:33])[CH2:26][C@@H:27]([CH:30]([CH3:32])[CH3:31])[CH:28]=[CH2:29])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

参加物

7

反応物 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 64800Benzenepropanoic acid, alpha-(phenylmethyl)-HCID 757711-HydroxybenzotriazoleHCID 178456019HCID 178456019、化合物

生成物 1

HCID 178455995HCID 178455995、化合物収率 42.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 83 mg (0.345 mmol) of dibenzylacetic acid, 90 mg (0.23 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2 -hydroxy-4-isopropyl-5-hexenyl]-imidazole-4-propionamide. 0.045 ml (0.345 mmol) of 4-ethylmorpholine, 93 mg (0.69 mmol) of HOBT and 85 mg (0.41 mmol) of DCC in 15 ml of dimethylformamide was stirred at room temperature overnight. Thereafter, the separated precipitate was filtered off and the filtrate was evaporated to dryness. The residue was then dissolved in ethyl acetate and the solution was washed in succession with 2N sodium bicarbonate solution, saturated ammonium chloride solution, again with 2N sodium bicarbonate solution and again with saturated ammonium chloride solution, dried over sodium sulfate and evaporated. The residue was chromatographed on 30 g of silica gel with a 14:1:0.1 mixture of methylene chloride, methanol and ammonia. Crystallization of the residue from methylene chloride/methanol/hexane yielded 60 mg of (S)-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2 -hydroxy-4-isopropyl-5-hexenyl]-α-(2,2-dibenzylacetamido)imidazole-4-propionamide, melting point 98°.

後処理

  1. filtrationThereafter, the separated precipitate was filtered off
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was then dissolved in ethyl acetate
  4. washthe solution was washed in succession with 2N sodium bicarbonate solution, saturated ammonium chloride solution, again with 2N sodium bicarbonate solution and again with saturated ammonium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on 30 g of silica gel with a 14:1:0.1 mixture of methylene chloride, methanol and ammonia
  8. customCrystallization of the residue from methylene chloride/methanol/hexane

出典と根拠

ORDレコード
ord-5abdb4f34cda4c20832ad0bb1abb777e
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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