Hydrochloric Acid → HCID 22271898, compound

HRID 488645Notes

Reaction equation

HRID 488645 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])(O)=O.[Na+].[CH3:25][O:26][C:27](Cl)=[O:28].Cl>O1CCOCC1>[CH3:25][O:26][C:27]([NH:16][CH:15]([CH2:14][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:17]([OH:19])=[O:18])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 69803277HCID 69803277, compound

Product 1

HCID 22271898HCID 22271898, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(4-nitro-1-naphthyl)alanine (0.65 g, 2.5 mmol), aqueous NaHCO3 (5 mL) and methylchloroformate (230 uL, 3 mmol, 1.2 eq) in dioxane (10 mL) was stirred for 3 hours, acidified to a ph <3 with aqueous 2N HCl and extracted with ethyl acetate. The combined organic layers was washed with water (1×25 mL), brine(1×25 mL), dried (MgSO4), filtered and concentrated under reduce pressure to provide the titled compound. MS (APCI(+)) m/e 319 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers was washed with water (1×25 mL), brine(1×25 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe1a71a0df874a3986d0caed1e8d8b0e
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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