Ethylmorpholine → HCID 178455995, 화합물

HRID 1655710노트

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HRID 1655710 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 178455995HCID 178455995, 화합물수율 42.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-5abdb4f34cda4c20832ad0bb1abb777e
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05250517

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