Trifluoroacetic acid → HCID 54017952, compound

HRID 1699274Notes

Reaction equation

HRID 1699274 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-5afd2dbcc6544defa5da8fc02f648ef0
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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