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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Dicyclohexylcarbodiimide → 17-Allyl-12-(2-(4-((-)-2-trifluoromethyl-2-methoxy-2-phenylacetoxy)-3-methoxycyclohexyl)-1-methylvinyl)-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo(22.3.1.04,9)octacos-18-ene-2, 3,10,16-tetraone

HRID 1439872
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HRID 1439872 반응식
[F:1][C:2]([F:16])([F:15])[C:3]([O:13][CH3:14])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:32][C@H:33]1[CH2:64][C:63]([CH3:65])=[CH:62][C@@H:61]([CH2:66][CH:67]=[CH2:68])[C:59](=[O:60])[CH2:58][C@H:57]([OH:69])[C@@H:56]([CH3:70])[C@@H:55](/[C:71](/[CH3:82])=[CH:72]/[C@H:73]2[CH2:78][C@@H:77]([O:79][CH3:80])[C@H:76](O)[CH2:75][CH2:74]2)[O:54][C:52](=[O:53])[C@H:51]2[N:46]([CH2:47][CH2:48][CH2:49][CH2:50]2)[C:44](=[O:45])[C:42](=[O:43])[C@:40]2([OH:83])[O:41][C@@H:36]([C@@H:37]([O:85][CH3:86])[CH2:38][C@H:39]2[CH3:84])[C@@H:35]([O:87][CH3:88])[CH2:34]1>C(OCC)(=O)C.CN(C1C=CN=CC=1)C.C(OCC)C>[CH2:66]([CH:61]1[CH:62]=[C:63]([CH3:65])[CH2:64][CH:33]([CH3:32])[CH2:34][CH:35]([O:87][CH3:88])[CH:36]2[O:41][C:40]([OH:83])([CH:39]([CH3:84])[CH2:38][CH:37]2[O:85][CH3:86])[C:42](=[O:43])[C:44](=[O:45])[N:46]2[CH:51]([CH2:50][CH2:49][CH2:48][CH2:47]2)[C:52](=[O:53])[O:54][CH:55]([C:71]([CH3:82])=[CH:72][CH:73]2[CH2:74][CH2:75][CH:76]([O:5][C:4](=[O:6])[C:3]([C:2]([F:15])([F:16])[F:1])([O:13][CH3:14])[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:77]([O:79][CH3:80])[CH2:78]2)[CH:56]([CH3:70])[CH:57]([OH:69])[CH2:58][C:59]1=[O:60])[CH:67]=[CH2:68]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 86531Mosher's acidHCID 445643Tacrolimus

생성물 1

HCID 5722415617-Allyl-12-(2-(4-((-)-2-trifluoromethyl-2-methoxy-2-phenylacetoxy)-3-methoxycyclohexyl)-1-methylvinyl)-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo(22.3.1.04,9)octacos-18-ene-2, 3,10,16-tetraone

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매
HCID 3283Diethyl Ether용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (-)-2-trifluoromethyl-2-methoxy-2-phenylacetic acid (51 mg) in ethyl acetate (10 ml) was added at room temperature N,N'-dicyclohexylcarbodiimide (47 mg). After stirring for 1.5 hours at room temperature, then the FR-900506 substance (25.0 mg) and 4-(N,N-dimethylamino)pyridine (11 mg) were added, followed by stirring at room temperature for 3.5 hours. The resulting solution was concentrated to provide a residue, which was taken up in diethyl ether and then washed successively with hydrochloric acid, an aqueous sodium hydrogen carbonate and an aqueous sodium chloride. The organic layer was dried over sodium sulfate and concentrated to provide a residue, which was chromatographed on silica gel (developing solvent: dichloromethane and diethyl ether, 10:1 v/v) to give 17-allyl-12-[2-[4-[(-)-2-trifluoromethyl-2-methoxy-2-phenylacetoxy]-3-methoxycyclohexyl]-1-methylvinyl]-1, 14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (6.5 mg) and 17-allyl-14-[(-)- 2-trifluoromethyl-2-methoxy-2-phenylacetoxy]-12-[2-[4-[(-)-2-trlfluoromethyl-2-methoxy-2-phenylacetoxy]-3-methoxycyclohexyl]-1-methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,91 ]octacos-18ene-2,3,10,16-tetraone (20.2 mg).

후처리

  1. stirringby stirring at room temperature for 3.5 hours
  2. concentrationThe resulting solution was concentrated
  3. customto provide a residue, which
  4. washwashed successively with hydrochloric acid
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customto provide a residue, which
  8. customwas chromatographed on silica gel (developing solvent: dichloromethane and diethyl ether, 10:1 v/v)

출처 및 근거

ORD 기록
ord-a7d998818795493288057d7338e55a1c
출처 데이터셋
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05496727

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