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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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4-Methylmorpholine → N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-b,b-dimethyl-D-phenylalanine

HRID 603902
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인쇄 미리보기

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HRID 603902 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:40])[CH2:11][S:12][C@H:13]3[C:16](=[O:17])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[C@@H:14]3[C:25]3[CH:39]=[CH:38][C:28]([O:29]CC(NCC(O)=O)=O)=[CH:27][CH:26]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C[N:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1.CN(C([O:55]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.FC(F)(F)C(O)=O.[CH3:77][C:78]([CH3:90])([C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1)[C@H:79]([C:81]([OH:83])=[O:82])[NH2:80]>CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:40])[CH2:11][S:12][C@H:13]3[C:16](=[O:17])[N:15]([C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)[C@@H:14]3[C:25]3[CH:39]=[CH:38][C:28]([O:29][CH2:44][C:43]([NH:42][CH2:47][C:46]([NH:80][C@@H:79]([C:81]([OH:83])=[O:82])[C:78]([CH3:90])([CH3:77])[C:84]4[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=4)=[O:45])=[O:55])=[CH:27][CH:26]=3)=[CH:9][C:4]=2[O:3][CH2:2]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66842897beta,beta-dimethyl-D-phenylalanine trifluoroacetateHCID 67271334N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycine

생성물 1

HCID 67271104
N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-b,b-dimethyl-D-phenylalanine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
30 °C

실험 절차

To a stirred solution of N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycine (15.6 mg, 0.027 mmol) in DMF (2 ml) was added N-methylmorpholine (15 μl, 0.091 mmol). TBTU (12.2 mg, 0.038 mmol) was added and the reaction mixture was stirred at 30° C. for 1 hour. β,β-dimethyl-D-phenylalanine trifluoroacetate (10.2 mg, 0.033 mmol) was added and the mixture was stirred at ambient temperature overnight. The solution was purified with preparative HPLC on a C8 column, UV 240/260 nm. A gradient from 20 to 45% MeCN in 0.1M NH4OAc buffer was used as eluent. The pure fractions were collected and the MeCN was removed under reduced pressure. The remaining water solution was acidified to pH 1 with HCl (1M) and extracted with DCM. The organic phase was passed through a phase separator and concentrated under reduced pressure. The residue was dissolved in MeCN and water. After lyophilisation, the title compound was obtained. H-NMR (400 MHz, DMSO-d6): 1.28 (d, 6H), 2.74-2.92 (m, 2H), 3.58-3.82 (m, 2H) 4.30-4.21 (m, 1H), 4.46 (s, 2H), 4.53-4.65 (m, 2H) 5.00 (b, 0.5H), 5.03 (b, 0.5H), 5.53 (b, 1H), 5.90-5.94 (m, 2H), 6.70-6.79 (m, 2H), 6.82 (s, 1H), 6.90-6.98 (m, 2H), 7.07-7.15 (m, 3H), 7.18-7.26 (m, 4H), 7.27-7.37 (m, 4H), 7.78 (b, 1H), 8.19 (t, 1H). M/z: 742.68 (M−1).

후처리

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. customThe solution was purified with preparative HPLC on a C8 column, UV 240/260 nm
  3. customThe pure fractions were collected
  4. customthe MeCN was removed under reduced pressure
  5. extractionextracted with DCM
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in MeCN

출처 및 근거

ORD 기록
ord-d401a8d447334797a4864bfa19e9ed8e
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07906502B2

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