3-(Trifluoromethyl)phenol → HCID 21921562, compound

HRID 1245097Notes

Reaction equation

HRID 1245097 reaction equation
FC1C=C[C:5]([C:6]([OH:8])=[O:7])=CC=1[N+]([O-])=O.F[C:15](F)(F)[C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][CH:21]=1.[N+:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=1)[C:31]([OH:33])=[O:32])([O-:27])=[O:26].CC(C)[N:50]=C=NC(C)C.[CH:57]1[CH:58]=[CH:59][C:60]2N(O)N=N[C:61]=2[CH:62]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[N+:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:45])([F:46])[F:47])[CH:39]=1)[C:31]([OH:33])=[O:32])([O-:27])=[O:26].[C:19]1([C:62]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:18]=[CH:17][C:16]([CH2:15][C@H:5]([NH:50][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:36]([O:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=3)=[C:28]([N+:25]([O-:27])=[O:26])[CH:29]=2)[C:6]([OH:8])=[O:7])=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 73763-(Trifluoromethyl)phenolHCID 12734DiisopropylcarbodiimideHCID 679874-Fluoro-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 21921562HCID 21921562, compound

Product 2

HCID 21921562HCID 21921562, compoundYield 81%HCID 58717697HCID 58717697, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

3-Nitro-4-(3-trifluoromethyl-phenoxy)-benzoic acid (530 mg, 81%) was prepared from 4-fluoro-3-nitro-benzoic acid (370 mg, 2.0 mmol) and 3-trifluoromethyl phenol (324 mg, 2.0 mmol) as in general procedure B. To Wang resin (60 mg, 0.06 mmol, 1.1 mmol/g) loaded with 4-L-biphenylalanine were added 82 mg of (0.25 mmol) 3-nitro-4-(3-trifluoromethyl-phenoxy)-benzoic acid (82 mg, 0.25 mmol), 1.0 M DIC (1.5 mL, 1.5 mmol) in DMF, 1.0 M HOBt (1.5 mL, 1.5 mmol) in DMF, and a catalytic amount of DMAP. The resulting mixture was left on shaker overnight. The resin was washed with DMF, MeOH, DCM three times of each and cleaved with 20% TFA in DCM. The residue obtained after removing the solvent was purified by chromatography to give the title compound (26 mg, 79%).

Workup

  1. washThe resin was washed with DMF, MeOH, DCM three times of each and
  2. customThe residue obtained
  3. customafter removing the solvent
  4. customwas purified by chromatography

Sources & evidence

ORD record
ord-db2cf75198264026bf372f0770fc85e4
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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