Hydrochloric Acid → HCID 12109161, compound

HRID 1274172Notes

Reaction equation

HRID 1274172 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[N+:28]([O-:30])=[O:29])[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[N+:28]([O-:30])=[O:29])[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 69823848HCID 69823848, compound

Product 1

HCID 12109161HCID 12109161, compoundYield 75.2%

Procedure

Benzyloxycarbonyl chloride (0.9 g) was dropwise added to an aqueous solution (10 ml) of (R)-4-(1-aminoethyl)-3-nitrobenzoic acid hydrochloride (1 g) and sodium hydroxide (535 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hours. Conc. hydrochloric acid was added to the reaction mixture to make the same acidic. The mixture was extracted with chloroform. The extract was washed with water, dried, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give 1.05 g of (R)-4-(1-benzyloxycarbonylaminoethyl)-3-nitrobenzoic acid.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-4421950599b1444c89bdb4a020edb4ce
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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