Hydrochloric Acid → HCID 12109155, compound

HRID 1274188Notes

Reaction equation

HRID 1274188 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[F: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[F: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 69823626HCID 69823626, compound

Product 1

HCID 12109155HCID 12109155, compoundYield 59%

Procedure

Benzyloxycarbonyl chloride (710 mg) was dropwise added to an aqueous solution (10 ml) of (R)-4-(1-aminoethyl)-3-fluorobenzoic acid hydrochloride (610 mg) and sodium hydroxide (390 mg), and the mixture was stirred at room temperature for 4 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 mixture was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=40:1) to give 520 mg of (R)-4-(1-benzyloxycarbonylaminoethyl)-3-fluorobenzoic acid.

Workup

  1. additionwas added to the reaction mixture
  2. extractionwas extracted with chloroform
  3. customThe mixture was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-88ee83b5014d4b6fa3be3a81b7f15d4a
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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