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Triethylamine → 5(S)-Tert-butoxycarbonylamino-4(S)-tert-butyldimethylsilyloxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(3-carbamoylpropyl)]-amide

HRID 725631
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HRID 725631 반응식
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH2:15])=[O:14].C(OP(C#N)(=O)OCC)C.[C:26]([O:30][C:31]([NH:33][C@@H:34]([CH2:50][C@@H:51]([CH:67]([CH3:69])[CH3:68])[CH2:52][C:53]1[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[C:55]([O:61][CH2:62][CH2:63][CH2:64][O:65][CH3:66])[CH:54]=1)[C@@H:35]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[CH2:36][C@@H:37]([CH3:41])[C:38](O)=[O:39])=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O>[C:13]([CH2:12][CH2:11][CH2:10][NH:9][C:38](=[O:39])[C@H:37]([CH3:41])[CH2:36][C@H:35]([O:42][Si:43]([C:46]([CH3:47])([CH3:49])[CH3:48])([CH3:45])[CH3:44])[C@@H:34]([NH:33][C:31]([O:30][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:32])[CH2:50][C@@H:51]([CH:67]([CH3:68])[CH3:69])[CH2:52][C:53]1[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[C:55]([O:61][CH2:62][CH2:63][CH2:64][O:65][CH3:66])[CH:54]=1)(=[O:14])[NH2:15]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 30147094-Aminobutyramide monohydrochlorideHCID 228658215(S)-tert-butoxycarbonylamino-4(S)-tert-butyldimethylsilyloxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxy-propyloxy)-phenyl]-octanoic acid

생성물 1

HCID 54231588
5(S)-Tert-butoxycarbonylamino-4(S)-tert-butyldimethylsilyloxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(3-carbamoylpropyl)]-amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

67 μl of triethylamine, 34 mg of 4-aminobutyric acid amide hydrochloride and 38 μl of cyanophosphonic acid diethyl ester are added in succession to 128 mg of 5(S)-tert-butoxycarbonylamino-4(S)-tert-butyldimethylsilyloxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxy-propyloxy)-phenyl]-octanoic acid in 8 ml of dimethylformamide at 0° C. The reaction mixture is stirred for a further 18 hours at room temperature. The reaction mixture is concentrated by evaporation and 20 ml of 10% citric acid solution and ice are added to the residue. The mixture is extracted repeatedly with ethyl acetate and the organic phases are then washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution. After concentration by evaporation, the residue is purified by means of FC (70 g of silica gel, dichloromethane/methanol=9:1). The title compound is obtained: Rf (dichloromethane/methanol=9:1)=0.38.

후처리

  1. concentrationThe reaction mixture is concentrated by evaporation and 20 ml of 10% citric acid solution and ice
  2. additionare added to the residue
  3. extractionThe mixture is extracted repeatedly with ethyl acetate
  4. washthe organic phases are then washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  5. concentrationAfter concentration
  6. customby evaporation
  7. customthe residue is purified by means of FC (70 g of silica gel, dichloromethane/methanol=9:1)

출처 및 근거

ORD 기록
ord-3e0e757c6d9c46e6ae10b88b75a3f236
출처 데이터셋
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05705658

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