Hydrochloric Acid → HCID 12109167, compound

HRID 1274178Notes

Reaction equation

HRID 1274178 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl.Cl.[NH2:16][C@@H:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=1[Cl:28])[CH3:18]>>[CH2:1]([O:8][C:9]([NH:16][C@@H:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=1[Cl:28])[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 69823416HCID 69823416, compound

Product 1

HCID 12109167HCID 12109167, compoundYield 69.7%

Procedure

Benzyloxycarbonyl chloride (750 mg) was dropwise added to an aqueous solution (10 ml) of (R)-4-(1-aminoethyl)-3-chlorobenzoic acid hydrochloride (690 mg) and sodium hydroxide (410 mg) at room temperature, and the mixture was stirred for 3 hours. After the reaction, conc. hydrochloric acid was added to the reaction mixture to make the same acidic, and the mixture was extracted with chloroform. The extract was dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give 680 mg of (R)-4-(1-benzyloxycarbonylaminoethyl)-3-chlorobenzoic acid.

Workup

  1. additionwas added to the reaction mixture
  2. extractionwas extracted with chloroform
  3. customThe extract was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-97e597a59ee84f109a9d57aeab24b04a
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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