Trifluoroacetic acid → HCID 13273048, compound

HRID 462721Notes

Reaction equation

HRID 462721 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[OH-].[Na+]>O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 132730475-Benzyloxy 1-para-aminophenyl 1-pentanone

Product 1

HCID 13273048HCID 13273048, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 16 g of formula (VIII) compound obtained in the preceding example and 21 g of triethylsilane were added 30.1 ml of trifluoroacetic acid and it was left under agitation for 20 hours at room temperature. Then, it was diluted with water, basified by means of concentrated NaOH, extracted with methylene chloride, washed with water, dried on sodium sulfate, the filtrate was evaporated and the residue chromatographed on a silica column [eluent: methylene chloride (99)-methanol (1) mixture]. Thus, 14 g of the expected compound were obtained in the form of an oil (Yield: 92%).

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with water
  3. customdried on sodium sulfate
  4. customthe filtrate was evaporated
  5. customthe residue chromatographed on a silica column [eluent: methylene chloride (99)-methanol (1) mixture]

Sources & evidence

ORD record
ord-06f3cc2b75464d05bd9199a7746d682e
Source dataset
uspto-grants-1985_05
Patent number
US04517197

Reaction notes

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