Hydrochloric Acid → HCID 13488124, compound

HRID 652279Notes

Reaction equation

HRID 652279 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:16]([CH2:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>[OH-].[Na+].O.C(OCC)C>[O:16]([CH2:23][C:24]([NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium Carbonate2×HCID 137064-Nitro-3-phenyl-L-alanineHCID 69703Phenoxyacetyl chloride

Product 1

HCID 13488124HCID 13488124, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Nitro-L-phenylalanine (21 g) was dissolved in 10% NaOH (10 ml), and an ethyl ether solution of phenoxyacetyl chloride (1.7 g) and an aqueous Na2CO3 solution prepared from Na2CO3 2.7 g and water 25 ml were alternately added stepwise thereto while stirring at room temperature over 20 minutes. After that, the mixture was stirred at a room temperature for 3 hours, and then acidified with dilute HCl to precipitate the crystals. The crystals were filtered, washed with water, and re-crystallized from dioxan to obtain N-phenoxyacetyl-4-nitro-L-phenylalanine as needles having melting point: 147° C. (2.4 g).

Workup

  1. additionwere alternately added stepwise
  2. stirringAfter that, the mixture was stirred at a room temperature for 3 hours
  3. customto precipitate the crystals
  4. filtrationThe crystals were filtered
  5. washwashed with water
  6. customre-crystallized from dioxan

Sources & evidence

ORD record
ord-e01049c351724db9b8c156cab1e279f1
Source dataset
uspto-grants-1987_06
Patent number
US04670584

Reaction notes

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