Trifluoroacetic acid → 2-Nitrophenol

HRID 1949614Notes

Reaction equation

HRID 1949614 reaction equation
C(O)(C(F)(F)F)=[O:2].C(O[C@@H](CCNC(OCC1C=CC=CC=1)=O)C(=O)[O:19][C:20]1[C:25](F)=[C:24](F)[C:23](F)=[C:22](F)[C:21]=1F)(=O)C1C=CC=CC=1.[NH4+:45].[OH-:46]>O>[N+:45]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[OH:19])([O-:2])=[O:46]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 58503143(S)-4-(benzyloxycarbonylamino)-1-oxo-1-(perfluorophenoxy)butan-2-yl benzoate

Product 1

HCID 69472-NitrophenolYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirring solution of TFA (1 mL) and water (0.2 mL) at 0° C. was added 3′,4′,3′″,4′″-tetra-deoxy-1-(N-Boc-2(S)-hydroxy-3-amino-propionyl)-neomycin (3, 0.164 mmol) and the reaction was stirred for 30 minutes, and checked for completeness by MS. Upon completion, the reaction was diluted with water (10 mL) and lyophilized to yield a crude, which was dissolved in conc. NH4OH (1.5 mL) and purified on a 1-inch reverse-phase HPLC column (0-10% ACN, 10 mM NH4OH) to yield 3′,4′,3′″,4′″-tetra-deoxy-1-(2(S)-hydroxy-3-amino-propionyl)-neomycin (4, 48.7 mg, 0.076 mmol, 40% yield): MS: m/z (M+H)+ calc. 638.0, obs.: 638.2; CLND 99.6% purity.

Workup

  1. customto yield a crude, which
  2. custompurified on a 1-inch reverse-phase HPLC column (0-10% ACN, 10 mM NH4OH)

Sources & evidence

ORD record
ord-fae8b37284df451488d315b094ecafcd
Source dataset
uspto-grants-2013_03
Patent number
US08399419B2

Reaction notes

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