Trifluoroacetic acid → benzyl (2S,3S)-3-hydroxy-2-(2-(3-nitro-5-(trifluoromethyl)benzamido)acetamido)hexyl(isobutyl)carba mate

HRID 2250803Notes

Reaction equation

HRID 2250803 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 86596713benzyl (2S,3S)-2-(2-aminoacetamido)-3-hydroxyhexyl(isobutyl)carbamate

Product 1

HCID 86596712benzyl (2S,3S)-3-hydroxy-2-(2-(3-nitro-5-(trifluoromethyl)benzamido)acetamido)hexyl(isobutyl)carba mate

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)carba mate (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-9785dac70f284de28514eede67742326
Source dataset
uspto-grants-2008_01
Patent number
US07317019B2

Reaction notes

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