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4-Methylmorpholine → 4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

HRID 446988
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HRID 446988 반응식
[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([OH:5])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[C:47]([O:51][C:52]([N:54]1[CH2:58][CH2:57][CH:56]2[NH:59][CH2:60][CH:61]([C:62](=[O:74])[NH:63][C:64]3[C:73]4[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=4)[CH:67]=[CH:66][CH:65]=3)[CH:55]12)=[O:53])([CH3:50])([CH3:49])[CH3:48]>CN1C(=O)CCC1.CCOC(C)=O>[C:47]([O:51][C:52]([N:54]1[CH2:58][CH2:57][CH:56]2[N:59]([C:3](=[O:5])[CH2:2][NH:1][C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])[CH2:60][CH:61]([C:62](=[O:74])[NH:63][C:64]3[C:73]4[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=4)[CH:67]=[CH:66][CH:65]=3)[CH:55]12)=[O:53])([CH3:50])([CH3:48])[CH3:49]
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참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672813746-(Naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 67281528
4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester
수율 73.5%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매2회

실험 절차

A solution of Cbz-Gly-OH (250 mg, 1.20 mmol) in NMP (2 mL) was cooled to 0° C. and treated with HATU (502 mg, 1.32 mmol) followed by NMM (0.2 mL). After 10 min, 54 (360 mg, 0.95 mmol) in NMP (2 mL) was added. The reaction mixture was allowed to warm to ambient temperature overnight. The solution was diluted with EtOAc, washed successively with 1M HCl, saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated. Purification by reverse phase HPLC (2″ Dynamax® C18, 10-70% ACN in H2O with 0.1% HOAc over 30 min) afforded 55 as a white solid (400 mg). Mass spectrum, m/z [573.2] (M+H)+.

후처리

  1. washwashed successively with 1M HCl, saturated NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by reverse phase HPLC (2″ Dynamax® C18, 10-70% ACN in H2O with 0.1% HOAc over 30 min)

출처 및 근거

ORD 기록
ord-deeb4adcd93b4d3b894c69432f1cf3cf
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481495B2

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