Hydrochloric Acid → HCID 22826056, compound

HRID 1903821Notes

Reaction equation

HRID 1903821 reaction equation
[CH3:1][C:2]1([CH3:29])[O:7][C:6]2[CH:8]=[C:9]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:10]=[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)[C:5]=2[C@@H:4]2[CH:24]=[C:25]([CH3:28])[CH2:26][CH2:27][C@@H:3]12.C(Cl)(=O)C(Cl)=O.[NH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1.Cl>C1C=CC=CC=1.[OH-].[Na+]>[CH3:29][C:2]1([CH3:1])[O:7][C:6]2[CH:8]=[C:9]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:10]=[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]([NH:36][CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=3)=[O:18])[C:5]=2[C@@H:4]2[CH:24]=[C:25]([CH3:28])[CH2:26][CH2:27][C@@H:3]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5610TyramineHCID 65578Oxalyl chlorideHCID 22826055HCID 22826055, compound

Product 1

HCID 22826056HCID 22826056, compoundYield 25.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 1.00 g (2.49 mmol) of (6aR-trans)-4-[(6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid in 4 ml of benzene was added 1.0 ml (1.46 g, 11.4 mmol) of oxalyl chloride. When the evolution of gas ceased, the mixture was heated with an 80° oil, both for 30 min. The excess oxalyl chloride and the benzene were evaporated under vacuum, 2 ml of benzene was added, and this was also evaporated. The residue was dissolved in 2 ml of ether and add with stirring to an ice cold solution of 443 mg (3.23 mmol) of tyramine in 3.25 nl of 1 N sodium hydroxide, while also adding, at the same rate, 2.5 ml of ice cold 1 N sodium hydroxide. The resulting suspension was stirred at ice temperature for one hour, acidified with hydrochloric acid and extracted with ether. The extracts were dried and concentrated, and the residue was chromatographed on silica gel. Elution with 2% methanol in chloroform and concentration of the fractions containing product gave 330 mg (25%) of (6aR-trans)-4-[(6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]butanamide as a colorless oil.

Workup

  1. temperaturethe mixture was heated with an 80° oil
  2. customThe excess oxalyl chloride and the benzene were evaporated under vacuum, 2 ml of benzene
  3. additionwas added
  4. customthis was also evaporated
  5. dissolutionThe residue was dissolved in 2 ml of ether
  6. additionadd
  7. extractionextracted with ether
  8. customThe extracts were dried
  9. concentrationconcentrated
  10. customthe residue was chromatographed on silica gel
  11. washElution with 2% methanol in chloroform and concentration of the fractions
  12. additioncontaining product

Sources & evidence

ORD record
ord-5b002fd11a684816b7bedf57d06d4b1d
Source dataset
uspto-grants-1984_03
Patent number
US04438207

Reaction notes

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