4-Methylmorpholine → 1-[[3-(acetylmercapto)-1-oxopropyl]amino]-L-proline

HRID 262702

反応式

HRID 262702 の反応式
[NH2:1][N:2]1[CH2:9][CH2:8][CH2:7][C@H:3]1[C:4]([OH:6])=[O:5].CN1[CH2:16][CH2:15][O:14]CC1.C(CC[C:22](Cl)=[S:23])(=O)C.[CH3:25][C:26](N(C)C)=[O:27]>>[C:26]([S:23][CH2:22][CH2:16][C:15]([NH:1][N:2]1[CH2:9][CH2:8][CH2:7][C@H:3]1[C:4]([OH:6])=[O:5])=[O:14])(=[O:27])[CH3:25]

参加物

5

反応物 4

HCID 79724-MethylmorpholineHCID 31374DimethylacetamideHCID 97357AminoprolineHCID 200413153-Acetylthiopropionyl chloride

生成物 1

HCID 141814621-[[3-(acetylmercapto)-1-oxopropyl]amino]-L-proline

実験手順

To a suspension of 3.9 g. of 1-amino-L-proline and 6.06 g. of N-methylmorpholine in 200 ml. of dimethylacetamide is added 4.98 g. of 3-acetylthiopropionyl chloride. The temperature of the reaction mixture rises to 34° spontaneously. The reaction mixture is then heated at 90° for 5 hours and allowed to cool to room temperature overnight. The crystalline solid, N-methylmorpholine hydrochloride, is removed by filtration and the filtrate concentrated under reduced pressure. The residue is dissolved in a minimum amount of 20% hydrochloric acid and the aqueous solution is then extracted with 3×150 ml. of ethyl acetate. The ethyl acetate extracts are combined, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to yield the desired 1-[[3-(acetylmercapto)-1-oxopropyl]amino]-L-proline.

後処理

  1. additionTo a suspension of 3.9 g
  2. customrises to 34°
  3. temperatureThe reaction mixture is then heated at 90° for 5 hours
  4. customThe crystalline solid, N-methylmorpholine hydrochloride, is removed by filtration
  5. concentrationthe filtrate concentrated under reduced pressure
  6. dissolutionThe residue is dissolved in a minimum amount of 20% hydrochloric acid
  7. extractionthe aqueous solution is then extracted with 3×150 ml
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-abcff77c11094cd39e9e530ebc1e51f7
出典データセット
uspto-grants-1979_05
特許番号
US04154934

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