Hydrochloric Acid → HCID 53946152, compound

HRID 1460486Notes

Reaction equation

HRID 1460486 reaction equation
[CH3:1][C@@:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][NH:3]1.[CH3:10][O:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][CH2:17]Br)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C.C(O)(=O)C>[CH3:10][O:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][CH2:17][N:3]2[CH2:4][CH2:5][CH2:6][C@@:2]2([CH3:1])[C:7]([OH:9])=[O:8])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 69936642-Methyl-L-proline

Product 1

HCID 53946152HCID 53946152, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of (S)-2-methylproline (1.47 g) (prepared by the method of D. Seebach et al., JACS, 105, 5390 (1983)), 4-methoxyphenethyl bromide (1.72 g) and sodium carbonate (2.12 g) in ethanol (30 ml) was heated under reflux for 48 hours, adjusted to pH8 with 2M hydrochloric acid, treated with glacial acetic acid to pH7, filtered and evaporated under reduced pressure. The residue was triturated with ethanol, filtered and evaporated under reduced pressure to give the title compound as a brown gum, (1.55 g), which was used directly in Preparation 10 without further purification.

Workup

  1. customprepared by the method of D
  2. temperatureunder reflux for 48 hours
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with ethanol
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d209e76a064147f6866c6ebab65bc881
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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