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Benzoic Acid → tert-butyl (2R,5R)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]-5-{[(phenylcarbonyl)amino]methyl}morpholine-4-carboxylate

HRID 629717
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HRID 629717 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][CH2:26][C@H:27]1[N:32]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][C@@H:30]([CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[NH:48][C:49](=[O:69])[C@H:50]([CH:56]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[NH:51][C:52]([O:54][CH3:55])=[O:53])[O:29][CH2:28]1.[C:70](O)(=[O:77])[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1.N1C(C)=CC=CC=1C>CN(C=O)C.CCOC(C)=O>[CH3:55][O:54][C:52]([NH:51][C@H:50]([C:49]([NH:48][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=1[CH2:41][CH2:40][C@H:30]1[O:29][CH2:28][C@@H:27]([CH2:26][NH:25][C:70]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)=[O:77])[N:32]([C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:31]1)=[O:69])[CH:56]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:53]
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참가 물질

7

반응물 4

HCID 243Benzoic AcidHCID 79372,6-LutidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86726318tert-butyl (2R,5R)-5-(aminomethyl)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate

생성물 1

HCID 86726321
tert-butyl (2R,5R)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]-5-{[(phenylcarbonyl)amino]methyl}morpholine-4-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

HATU (1.4 eq) was added to a stirred mixture a solution of tert-butyl (2R,5R)-5-(aminomethyl)-2-[2-(2-{[N-(methoxycarbonyl)-β-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate (1 eq), benzoic acid (1.2 eq) and 2,6-lutidine (2 eq) in DMF (0.05 M) and the mixture was stirred at room temperature for 16 hrs. The mixture was diluted in EtOAc, The organic layer was washed with aqueous saturated NH4Cl and brine. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by automated silica gel flash chromatography system eluted with a gradient 10% to 100% of EtOAc/Hex to afford title compound.

후처리

  1. washThe organic layer was washed with aqueous saturated NH4Cl and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by automated silica gel flash chromatography system
  6. washeluted with a gradient 10% to 100% of EtOAc/Hex

출처 및 근거

ORD 기록
ord-c905608802e1452aae03d8e16cc1bedc
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315475B2

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