Trifluoroacetic acid → HCID 54017952, compound

HRID 1782733Notes

Reaction equation

HRID 1782733 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([CH2:9][C@@H:10]([NH:24]C(OC(C)(C)C)=O)[CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:4][C:3]=1[Br:32].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:24][C@H:10]([CH2:9][C:5]1[CH:6]=[C:7]([Br:8])[C:2]([NH2:1])=[C:3]([Br:32])[CH:4]=1)[CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68855098HCID 68855098, compound

Product 1

HCID 54017952HCID 54017952, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a mixture of 4 g (7 mmol) of (R)-1-[3-(4-amino-3,5-dibromophenyl)-2-[N-[(1,1-dimethylethoxy)carbonyl]-amino]propyl]-4-(1-piperidinyl)-piperidine and 100 ml of methylene chloride, 40 ml of trifluoroacetic acid were slowly added dropwise, with stirring, at 10° C. The reaction mixture was stirred for 2 hours at room temperature and then evaporated down in vacuo. The residue was mixed with ice water, made basic by the addition of concentrated aqueous ammonia solution and extracted three times with 200 ml of diethylether. The combined ether extracts were dried and evaporated down in vacuo. 3.4 g (100% of theory) of an amorphous solid were obtained.

Workup

  1. additionwere slowly added dropwise
  2. stirringThe reaction mixture was stirred for 2 hours at room temperature
  3. customevaporated down in vacuo
  4. additionThe residue was mixed with ice water
  5. additionmade basic by the addition of concentrated aqueous ammonia solution
  6. extractionextracted three times with 200 ml of diethylether
  7. dry with materialThe combined ether extracts were dried
  8. customevaporated down in vacuo
  9. custom3.4 g (100% of theory) of an amorphous solid were obtained

Sources & evidence

ORD record
ord-2d6422f61e6349b2ba5da6967bd16711
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

Loading…