Hydrochloric Acid → (S)-2-[[(2,6-dichloro-3-nitrophenyl)methyl]amino]propanamide

HRID 326889Notes

Reaction equation

HRID 326889 reaction equation
Br.[NH2:2][C@@H:3]([CH3:7])[C:4]([NH2:6])=[O:5].C([O-])(=O)C.[Na+].[Cl:13][C:14]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([Cl:25])[C:15]=1[CH:16]=O.[B-]C#N.[Na+].Cl>CO>[Cl:13][C:14]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([Cl:25])[C:15]=1[CH2:16][NH:2][C@@H:3]([CH3:7])[C:4]([NH2:6])=[O:5]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 27949122,6-Dichloro-3-nitrobenzaldehydeHCID 18632422L-Alaninamide--hydrogen bromide (1/1)HCID 20587905Sodium cyanoborohydride [MI]

Product 1

HCID 9971552(S)-2-[[(2,6-dichloro-3-nitrophenyl)methyl]amino]propanamideYield 70.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a homogeneous solution of 8.42 parts of (S)-2-aminopropanamide monohydrobromide, 12.26 parts of sodium acetate and 79 parts of methanol there were added 10.96 parts of 2,6-dichloro-3-nitrobenzaldehyde and, after 1/2 hour, a mixture of 3.77 parts of sodium cyanotrihydroborate and 7.9 parts of methanol. The whole was stirred for 45 min at room temperature. After acidifying to pH 1 with HCl (3N), stirring was continued overnight. The reaction mixture was evaporated and the residue was basified with NaHCO3 (sat.). The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was recrystallized from 2-propanol, yielding 10.29 parts (70.7%) of (S)-2-[[(2,6-dichloro-3-nitrophenyl)methyl]amino]propanamide (interm. 69).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe reaction mixture was evaporated
  4. extractionThe product was extracted with dichloromethane
  5. customthe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-1381cb406f7a48efa44f4b31bfca75af
Source dataset
uspto-grants-1993_12
Patent number
US05270464

Reaction notes

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