Ammonia → HCID 58123695, compound

HRID 536669Notes

Reaction equation

HRID 536669 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[NH2:7][C:8]1[C:29]([OH:30])=[CH:28][C:11]2[CH2:12][C@@H:13]3[C:18]([CH3:20])([CH3:19])[C@:17]([CH3:21])([C:10]=2[CH:9]=1)[CH2:16][CH2:15][N:14]3[C:22](=[O:27])[C:23]([F:26])([F:25])[F:24].C(N(CC)CC)C.N>ClCCl.CO>[OH:30][C:29]1[C:8]([NH:7][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])=[CH:9][C:10]2[C@@:17]3([CH3:21])[C:18]([CH3:20])([CH3:19])[C@H:13]([N:14]([C:22](=[O:27])[C:23]([F:26])([F:24])[F:25])[CH2:15][CH2:16]3)[CH2:12][C:11]=2[CH:28]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 58123690HCID 58123690, compound

Product 1

HCID 58123695HCID 58123695, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Cyclopropylcarbonyl chloride (0.13 mL) is added to a solution of 1-[(2R,6S)-8-amino-9-hydroxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-2,2,2-trifluoro-ethanone (0.50 g) and triethylamine (0.25 mL) in dichloromethane (3 mL). After stirring the solution at room temperature overnight, concentrated aqueous ammonia solution (1 mL) and methanol (2 mL) are added and the resulting mixture is stirred for additional 2 h. Then, the solution is concentrated and water is added to the residue. The resulting mixture is extracted with ethyl acetate and the combined organic extracts are washed with brine and dried (MgSO4). The solvent is removed under reduced pressure to give the crude title compound that is used without further purification.

Workup

  1. additionare added
  2. concentrationThen, the solution is concentrated
  3. additionwater is added to the residue
  4. extractionThe resulting mixture is extracted with ethyl acetate
  5. washthe combined organic extracts are washed with brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-10fbf455d57940aa91393a16c93cbaa3
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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