Ammonia → HCID 68855917, compound

HRID 1699275Notes

Reaction equation

HRID 1699275 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([Br:17])[C:14]=1[O:15][CH3:16])[CH2:6][C@H:7]([C:9]([OH:11])=[O:10])[NH2:8].[CH3:18]O.Cl.N>ClCCl.C(OCC)(=O)C.C1CCCCC1.CO>[CH3:18][NH:8][C@@H:7]([C:9]([OH:11])=[O:10])[CH2:6][C:5]1[CH:4]=[C:3]([Br:2])[C:14]([O:15][CH3:16])=[C:13]([Br:17])[CH:12]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 887MethanolHCID 22945655HCID 22945655, compound

Product 1

HCID 68855917HCID 68855917, compound

Reagents, catalysts & solvents 1

HCID 86583941HCID 86583941, compoundSolvent

Procedure

To a mixture of 5.5 g (14.12 mmol) of 3,5-dibromo-4-methoxy-D-phenylalanine-hydrochloride and 55 ml of methanol were added 150 ml of a saturated methanolic hydrogen chloride solution and the mixture was stirred for 20 hours at room temperature. The residue remaining after evaporation of the solvent was stirred with 50 ml of water and adjusted to pH 8 with saturated sodium hydrogen carbonate solution. The precipitate was suction filtered, stirred with 10 ml of isopropanol and left to stand overnight. The insoluble matter was filtered off and the filtrate was evaporated down in vacuo. The residue was further reacted as a crude product. Yield: 1.0 g (28.7% of theory) of a colourless oil , Rf=0.55 (eluant: dichloromethane/ethyl acetate/cyclohexane/methanol/conc. ammonia=300/80/25/25/3 (v/v/v/v/v)).

Workup

  1. customafter evaporation of the solvent
  2. stirringwas stirred with 50 ml of water
  3. filtrationfiltered
  4. stirringstirred with 10 ml of isopropanol
  5. waitleft
  6. waitto stand overnight
  7. filtrationThe insoluble matter was filtered off
  8. customthe filtrate was evaporated down in vacuo
  9. customThe residue was further reacted as a crude product

Sources & evidence

ORD record
ord-f915060477394409aefb01f25800bf0f
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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