4-Methylmorpholine → {1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester

HRID 446990노트

반응식

HRID 446990 반응식
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[C:3]([CH3:6])([CH3:5])[CH3:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[CH2:48]([O:55][C:56](=[O:82])[NH:57][CH2:58][C:59]([N:61]1[CH2:65][CH:64]([C:66](=[O:78])[NH:67][C:68]2[C:77]3[C:72](=[CH:73][CH:74]=[CH:75][CH:76]=3)[CH:71]=[CH:70][CH:69]=2)[CH:63]2[NH:79][CH2:80][CH2:81][CH:62]12)=[O:60])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN1C(=O)CCC1.CCOC(C)=O>[C:13]([O:12][C:10](=[O:11])[NH:1][CH:2]([C:7]([N:79]1[CH2:80][CH2:81][CH:62]2[N:61]([C:59](=[O:60])[CH2:58][NH:57][C:56]([O:55][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:82])[CH2:65][CH:64]([C:66](=[O:78])[NH:67][C:68]3[C:77]4[C:72](=[CH:73][CH:74]=[CH:75][CH:76]=4)[CH:71]=[CH:70][CH:69]=3)[CH:63]12)=[O:9])[C:3]([CH3:4])([CH3:5])[CH3:6])([CH3:16])([CH3:15])[CH3:14]

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67280980{2-[3-(Naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

생성물 1

HCID 67282206{1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester수율 109.4%

시약·촉매·용매 2

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

실험 절차

A solution of Boc-Tle-OH (176 mg, 0.76 mmol) in NMP (3 mL) was cooled to 0° C. and treated with HATU (318 mg, 0.83 mmol) followed by NMM (0.15 mL). After 10 min, 56 (360 mg, 0.76 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 to afford 57 (570 mg) which was used without further purification. Mass spectrum, m/z [686.4] (M+H)+.

후처리

  1. washwashed successively with 1M HCl, saturated NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-db4fd30ef2a846c5999572eecb79810b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481495B2

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