Trifluoroacetic acid → HCID 53855375, compound

HRID 850632Notes

Reaction equation

HRID 850632 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@@H:10]([N:15]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([NH:29]CC4C=CC(OC)=CC=4)[N:24]=3)[C:16]2=[O:39])[CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[N:8][CH:9]=1)[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[NH2:29][C:25]1[N:24]=[C:23]([CH2:22][CH2:21][CH2:20][N:17]2[CH2:18][CH2:19][N:15]([C@H:10]([C:6]3[CH:7]=[N:8][CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)[CH2:11][C:12]([OH:14])=[O:13])[C:16]2=[O:39])[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54293955HCID 54293955, compound

Product 1

HCID 53855375HCID 53855375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 20-13 (0.031 g, 0.052 mmol) in dichloromethane (10 mL) was added TFA (1 mL). The solution was stirred for 16 hours at 85° C. after which the solvent was removed in vacuo and azeotroped twice with toluene (15 mL). The residue was chromatographed (silica gel, 15:10:1:1 followed by 10:10:1:1 ethyl acetate/EtOH/water/NH4OH) to give 20-14 as a white solid.

Workup

  1. customwas removed in vacuo
  2. customazeotroped twice with toluene (15 mL)
  3. customThe residue was chromatographed (silica gel, 15:10:1:1 followed by 10:10:1:1 ethyl acetate/EtOH/water/NH4OH)

Sources & evidence

ORD record
ord-757fd1d53c654d919f733dfb9b548a76
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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