Trifluoroacetic acid → Trifluoroacetate

HRID 525265Notes

Reaction equation

HRID 525265 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:18]=[C:17]3[C:12]([N:13]=[CH:14][CH:15]=[N:16]3)=[C:11]([NH:19][CH:20]3[CH2:25][CH2:24][CH:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22][CH2:21]3)[CH:10]=1)[CH2:2]2.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>C(Cl)Cl>[CH:5]12[O:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:9]1[CH:18]=[C:17]3[C:12]([N:13]=[CH:14][CH:15]=[N:16]3)=[C:11]([NH:19][CH:20]3[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]3)[CH:10]=1)[CH2:4]2.[F:37][C:36]([F:39])([F:38])[C:34]([O-:40])=[O:35]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86282390HCID 86282390, compound

Product 2

HCID 84468TrifluoroacetateHCID 117604750HCID 117604750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As shown in step 4-iii of Scheme 4, to a solution of compound 1007 (141 mg, 0.295 mmol) in CH2Cl2 (2.5 mL) was added TFA (656 mg, 443 μL, 5.75 mmol) at RT. The resulting black solution was stirred for 2 hours and then the reaction was quenched by the addition of saturated NaHCO3 until the black color gradually turned into an orange color. The reaction mixture was extracted with CH2Cl2 (3×) and the combined organic extracts were dried over Na2SO4 and evaporated to dryness to provide N1-(7-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)quinoxalin-5-yl)cyclohexane-1,4-diamine, trifluoroacetate (compound 1008): ESMS (M+H+)=354.20. This material was used in subsequent reactions without any further purification.

Workup

  1. customthe reaction was quenched by the addition of saturated NaHCO3 until the black color
  2. extractionThe reaction mixture was extracted with CH2Cl2 (3×)
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-25f8eefea06d479ebd1baf1b062b0313
Source dataset
uspto-grants-2016_05
Patent number
US09340557B2

Reaction notes

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