Trifluoroacetic acid → HCID 86596712, 화합물

HRID 251320

반응식

HRID 251320 반응식
C(O)(C(F)(F)F)=O.[NH2:8][CH2:9][C:10]([NH:12][C@H:13]([C@@H:30]([OH:34])[CH2:31][CH2:32][CH3:33])[CH2:14][N:15]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:11].C(N(CC)C(C)C)(C)C.[N+:44]([C:47]1[CH:48]=[C:49]([CH:53]=[C:54]([C:56]([F:59])([F:58])[F:57])[CH:55]=1)[C:50](O)=[O:51])([O-:46])=[O:45].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CN(C=O)C>[OH:34][C@@H:30]([CH2:31][CH2:32][CH3:33])[C@@H:13]([NH:12][C:10](=[O:11])[CH2:9][NH:8][C:50](=[O:51])[C:49]1[CH:53]=[C:54]([C:56]([F:59])([F:58])[F:57])[CH:55]=[C:47]([N+:44]([O-:46])=[O:45])[CH:48]=1)[CH2:14][N:15]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86596713HCID 86596713, 화합물

생성물 1

HCID 86596712HCID 86596712, 화합물

시약·촉매·용매 1

HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

A solution of the TFA salt of benzyl (2S,3S)-2-(2-aminoacetamido)-3-hydroxyhexyl(isobutyl)carbamate in 1:1 CH2Cl2/DMF was charged successively with N,N-diisopropylethylamine (0.139 mL), 3-nitro-5-trifluoromethylbenzoic acid (39 mg), and HATU (90 mg). The reaction was stirred for 14 h at RT before being partitioned between EtOAc and water. The organic phase was washed with sat. NH4Cl, water, and brine before being dried (Na2SO4), filtered, and concentrated in vacuo to afford benzyl (2S,3S)-3-hydroxy-2-(2-(3-nitro-5-(trifluoromethyl)benzamido)acetamido)hexyl(isobutyl)carbamate (94 mg), which was taken onto the next step without further purification. MS found: (M+H)+=597.2.

후처리

  1. custombefore being partitioned between EtOAc and water
  2. washThe organic phase was washed with sat. NH4Cl, water, and brine
  3. dry with materialbefore being dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6caf5414c7f44477b6bee6c9a785efd6
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863333B2

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