Trifluoroacetic acid → HCID 86596712, compound

HRID 251320

Reaction equation

HRID 251320 reaction equation
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

Participants

7

Reactant 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, compound

Product 1

HCID 86596712HCID 86596712, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6caf5414c7f44477b6bee6c9a785efd6
Source dataset
uspto-grants-2011_01
Patent number
US07863333B2

Linked notes

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