1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(6-(benzyloxy)-6-oxohexylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate

HRID 2205003노트

반응식

HRID 2205003 반응식
[C:1]([O:14][C@H:15]([CH2:41][O:42][C:43](=[O:55])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:16][S:17][CH2:18][C@@H:19]([C:38](O)=[O:39])[NH:20][C:21](=[O:37])[O:22][CH2:23][CH:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][C:93]([O:95][CH2:96][C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=1)=[O:94]>CN(C=O)C.C(OCC)(=O)C>[C:43]([O:42][CH2:41][C@@H:15]([O:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:16][S:17][CH2:18][C@H:19]([NH:20][C:21]([O:22][CH2:23][CH:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:37])[C:38]([NH:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][C:93]([O:95][CH2:96][C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=1)=[O:94])=[O:39])(=[O:55])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67401791Benzyl 6-aminohexanoate hydrochlorideHCID 67414703(5R,9R)-9-(dodecanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylic acid

생성물 1

HCID 86678291(R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(6-(benzyloxy)-6-oxohexylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (5R,9R)-9-(dodecanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylic acid (6, 1 eq) in DMF (0.2 M) was added DIEA (5 eq) and EDCI (1.3 eq) and HOBT (1.3 eq). The reaction was stirred at room temperature for 10 minutes, which was followed by adding benzyl 6-aminohexanoate hydrochloride (1.2 eq). The reaction mixture was then stirred at room temperature overnight. The mixture was diluted with ethyl acetate, and washed with saturated NaHCO3 solution, water and brine. The organic layer was dried over anhydrous Na2SO4, and concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give the title product.

후처리

  1. stirringThe reaction mixture was then stirred at room temperature overnight
  2. washwashed with saturated NaHCO3 solution, water and brine
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated en vaccuo
  5. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)

출처 및 근거

ORD 기록
ord-5589d8d665b541b1ac321c15f2093973
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365506B2

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