Hydrochloric Acid → HCID 86742681, compound

HRID 2292070Notes

Reaction equation

HRID 2292070 reaction equation
C(O)(=O)C(O)=O.[Cl:7][C:8]1[N:13]=[C:12]([C@H:14]([OH:33])[CH2:15][NH:16][C@H:17]([CH3:32])[CH2:18][C:19]2[CH:31]=[CH:30][C:22]([C:23]([CH3:29])=[CH:24][C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=2)[CH:11]=[CH:10][CH:9]=1.[OH-].[K+].Cl>O>[ClH:7].[Cl:7][C:8]1[N:13]=[C:12]([C@H:14]([OH:33])[CH2:15][NH:16][C@H:17]([CH3:32])[CH2:18][C:19]2[CH:31]=[CH:30][C:22]([C:23]([CH3:29])=[CH:24][C:25]([OH:27])=[O:26])=[CH:21][CH:20]=2)[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86742682HCID 86742682, compound

Product 1

HCID 86742681HCID 86742681, compoundYield 133.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 958 mg of methyl p-[(R)-2-[[(R)-2-(6-chloro-2-pyridyl)-2-hydroxyethyl]amino]propyl]-β-methylcinnamate oxalate (Example 2Ga), 60 ml of 5% methanolic KOH and 10 ml of water were heated to 50° under argon while stirring for 3 hours. For the working-up, the mixture was diluted with water, adjusted to pH 5 with 2N hydrochloric acid and extracted repeatedly with ethyl acetate. The combined extracts were dried and evaporated in a vacuum. There were obtained 550 mg of amorphous p-[(R)-2-[[(R)-2-(6-chloro-2-pyridyl)-2-hydroxyethyl]amino]propyl]-β-methylcinnamic acid hydrochloride, [α]D20 =-45° (c=0.5 in MeOH).

Workup

  1. extractionextracted repeatedly with ethyl acetate
  2. customThe combined extracts were dried
  3. customevaporated in a vacuum

Sources & evidence

ORD record
ord-9175437de9564d469c56affa356ce5a5
Source dataset
uspto-grants-1989_01
Patent number
US04800206

Reaction notes

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