Trifluoroacetic acid → HCID 59843177, compound

HRID 2196532Notes

Reaction equation

HRID 2196532 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][CH:34]=[CH:33][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[N:13]([C:14]2[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=2)[CH2:17][NH:18]C(=O)OC(C)(C)C)[N:12]=[C:11]([C:29]([F:32])([F:31])[F:30])[CH:10]=1)=[O:8].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:18][CH2:17][C:16]1[CH:15]=[C:14]([N:13]2[C:9]([C:7]([NH:6][CH2:5][C:4]3[CH:33]=[CH:34][CH:35]=[CH:36][C:3]=3[O:2][CH3:1])=[O:8])=[CH:10][C:11]([C:29]([F:31])([F:32])[F:30])=[N:12]2)[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69096436HCID 69096436, compound

Product 1

HCID 59843177HCID 59843177, compoundYield 128.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
21 °C

Procedure

To a stirred solution of 57 (900 mg, 1.784 mmol) in CH2Cl2 (3.4 mL) was added TFA (2.8 mL, 35.7 mmol). The mixture was allowed to stir at 21° C. for 2 h. A saturated NaHCO3 aqueous solution was added and followed by extractions with CH2Cl2. It was then dried over Na2SO4 and evaporated. The crude was used without any further purification. The title product 58 (925 mg, 100% yield) was isolated as a beige powder. LRMS (ESI): calc. 404.4; found 405.6 (MH)+.

Workup

  1. extractionfollowed by extractions with CH2Cl2
  2. dry with materialIt was then dried over Na2SO4
  3. customevaporated
  4. customThe crude was used without any further purification

Sources & evidence

ORD record
ord-21f9543c8cc64cdc87c9f24a56326649
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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