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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Trifluoroacetic acid → N-{[4-((2R,3R)-1-(4-Fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethy]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-alanyl-D-valine

HRID 254029
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HRID 254029 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[O:16])[C@H:9]2[C:24]2[CH:39]=[CH:38][C:27]([O:28][CH2:29][C:30]([NH:32][C@H:33]([C:35]([OH:37])=O)[CH3:34])=[O:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.Cl.C([O:45][C:46](=[O:52])[C@@H:47]([CH:49]([CH3:51])[CH3:50])[NH2:48])(C)(C)C.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(O)(C(F)(F)F)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[OH:16])[C@H:9]2[C:24]2[CH:25]=[CH:26][C:27]([O:28][CH2:29][C:30]([NH:32][C@H:33]([C:35]([NH:48][C@@H:47]([C:46]([OH:52])=[O:45])[CH:49]([CH3:51])[CH3:50])=[O:37])[CH3:34])=[O:31])=[CH:38][CH:39]=2)=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 45108216H-D-Val-OtBu hydrochlorideHCID 66842883N-{[4-((2R,3R)-1-(4-Fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-alanine

생성물 1

HCID 66842877
N-{[4-((2R,3R)-1-(4-Fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethy]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-alanyl-D-valine
수율 79.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

A solution of N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-([2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-alanine (0.015 g, 0.027 mmol), D-valine tert-butyl ester hydrochloride (0.008 g, 0.038 mmol) and N-methylmorpholine (0.030 ml, 0.272 mmol) in DCM (4 ml) was stirred for 5 min. TBTU (0.013 g, 0.041 mmol) was added. After 3 h, the conversion to the ester (M/z: 710.2) was completed and TFA (3 ml) was added. After 4 h, the mixture was diluted with toluene (2 ml) and the solvent was removed under reduced pressure. The residue was dissolved in MeOH (4 ml) and NaBH4 was added in small portions to the solution (a total of 0.065 g, 1.72 mmol) until the reduction was complete. Ammonium acetate buffer (0.1M, 3 ml) was added and most of the methanol was removed under reduced pressure. The remaining solution was purified by preparative HPLC, using a gradient of 20-50% MeCN in a 0.1M ammonium acetate buffer as eluent. After freeze-drying, 0.014 g (77% yield) of the title compound was obtained as a white solid. M/z: 656.1. 1H NMR (DMSO, 400 MHz): δ 0.75-0.83 (m, 6H), 1.22 (d, 3H), 1.95-2.07 (m, 1H), 3.83-3.96 (m, 2H), 3-98-4.06 (m, 1H), 4-24-4.31 (m, 1H), 4.40-4.54 (m, 3H), 4.67-4.76 (m, 1H), 5.01-5.07 (m, 1H), 6.91-7.98 (m, 2H), 7.05-7.17 (m, 4H), 7.19-7.25 (m, 2H), 7.29-7.39 (m, 4H), 7.84-7.95 (m, 1H). 8.07 (d, 1H),

후처리

  1. waitAfter 4 h
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in MeOH (4 ml)
  4. additionNaBH4 was added in small portions to the solution (a total of 0.065 g, 1.72 mmol) until the reduction
  5. additionAmmonium acetate buffer (0.1M, 3 ml) was added and most of the methanol
  6. customwas removed under reduced pressure
  7. customThe remaining solution was purified by preparative HPLC
  8. customAfter freeze-drying

출처 및 근거

ORD 기록
ord-d1d1d9e048a64a2c9b8d87a6ba1383f9
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07871998B2

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