HCID 117857251, compound → HCID 86582906, compound

HRID 1483158Notes

Reaction equation

HRID 1483158 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]([C:9]1[CH:27]=[CH:26][C:12]2[CH2:13][C@@H:14]3[C@H:19]([CH3:20])[C@:18]([CH3:21])([C:11]=2[CH:10]=1)[CH2:17][CH2:16][N:15]3[CH2:22][CH2:23][O:24][CH3:25])=[O:8]>FC(F)(F)C(O)=O>[CH3:25][O:24][CH2:23][CH2:22][N:15]1[CH2:16][CH2:17][C@:18]2([CH3:21])[C@@H:19]([CH3:20])[C@H:14]1[CH2:13][C:12]1[CH:26]=[CH:27][C:9]([C:7]([NH2:6])=[O:8])=[CH:10][C:11]=12

Participants

3

Reactant 1

HCID 117857251HCID 117857251, compound

Product 1

HCID 86582906HCID 86582906, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of (2R,6R,11R)-N-(2,4-dimethoxybenzyl)-3-(2-methoxyethyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocine-8-carboxamide (360 mg, 0.80 mmol) in trifluoroacetic acid (5 mL) was stirred at ambient temperature for 2 hours. The mixture was concentrated under reduced pressure before quenching with ice/ammonium hydroxide (28%) (25 mL). The crude product was extracted twice to using dichloromethane (100 mL) and the combined organic layers dried (MgSO4). Filtration and removal of the solvent under reduced pressure gave the crude product that was purified by prep-HPLC giving (2R,6R,11R)-3-(2-methoxyethyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocine-8-carboxamide (130 mg, 54% yield); LC/MS (M+H)+=303.2.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custombefore quenching with ice/ammonium hydroxide (28%) (25 mL)
  3. extractionThe crude product was extracted twice
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. filtrationFiltration and removal of the solvent under reduced pressure
  6. customgave the crude product that
  7. customwas purified

Sources & evidence

ORD record
ord-5fe7d51a22254ae7b80a9a595d1ee500
Source dataset
uspto-grants-2016_08
Patent number
US09416137B2

Reaction notes

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