Trifluoroacetic acid → HCID 86586710, compound

HRID 2088174Notes

Reaction equation

HRID 2088174 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@@H:14]([C:16]([O:18]C(C)(C)C)=[O:17])[CH2:15][C@@:9]1([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:10]([O:23][CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=1)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.Cl.[NH2:53][NH:54][C:55]([NH2:57])=[O:56].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[NH2:53][NH:54][C:55]([NH2:57])=[O:56].[CH2:1]([N:8]1[C@@H:13]2[C@@H:14]([C:16]([OH:18])=[O:17])[CH2:15][C@@:9]1([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:10]([O:23][CH2:24][C:25]1[CH:26]=[C:27]([C:35]([F:37])([F:38])[F:36])[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 11236Semicarbazide hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86586645HCID 86586645, compound

Product 1

HCID 86586710HCID 86586710, compoundYield 108.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (1R*,2R*,5S*,6S*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Description 22; 250 mg, 0.4 mmol), trifluoroacetic acid (0.8 ml) and dichloromethane (1.2 ml) was stirred at room temperature overnight and concentrated in vacuo. The residue was treated with semicarbazide hydrochloride (355 mg, 3.2 mmol), triethylamine (1 ml, 7.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (457 mg, 4.2 mmol), and 4-N,N-dimethylaminopyridine (35 mg, 0.28 mmol). The mixture was stirred at room temperature over weekend, quenched with saturated aqueous NaHCO3 and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol:ammonia) to give the title compound (278 mg, 55%).

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe mixture was stirred at room temperature over weekend
  3. customquenched with saturated aqueous NaHCO3
  4. extractionextracted into dichloromethane
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol:ammonia)

Sources & evidence

ORD record
ord-3fbf3a908dd146ccb45260464d6ae06b
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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