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

HRID 1491631ノート

反応式

HRID 1491631 の反応式
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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1b7705a64d1b4c8e9c75443c68df2631
出典データセット
uspto-grants-1994_12
特許番号
US05371079

反応ノート

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