Ethylmorpholine → N-ethoxycarbonyl-L-alanyl-L-proline ethylamide

HRID 47046ノート

反応式

HRID 47046 の反応式
Br.[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13])[CH3:3].C(N1CCOCC1)C.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27]>O1CCCC1>[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:3]

参加物

5

反応物 3

HCID 7525EthylmorpholineHCID 10928Ethyl chloroformateHCID 70602162L-alanyl-L-proline ethylamide hydrobromide

生成物 1

HCID 54402446N-ethoxycarbonyl-L-alanyl-L-proline ethylamide収率 47%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2 g (0.0066 mol) of L-alanyl-L-proline ethylamide hydrobromide were suspended in 20 ml of dry tetrahydrofuran, 1.84 ml (0.0145 mol) of N-ethylmorpholine and 0.76 ml (0.0079 mol) of ethyl chloroformate were added and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated off and the residue dissolved in 100 ml of chloroform and washed successively with 2-N hydrochloric acid in brine, brine, saturated sodium bicarbonate solution and brine, dried over magnesium sulphate and evaporated to an oil which soon crystallised. Recrystallisation from chloroform/petrol yielded 0.88 g (47%) of N-ethoxycarbonyl-L-alanyl-L-proline ethylamide of melting point 126°-128° C.; [α]D20 =-117.6° (c=1.02% in methanol).

後処理

  1. customThe solvent was evaporated off
  2. dissolutionthe residue dissolved in 100 ml of chloroform
  3. washwashed successively with 2-N hydrochloric acid in brine, brine, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to an oil which
  6. customsoon crystallised
  7. customRecrystallisation from chloroform/petrol

出典と根拠

ORDレコード
ord-3b7eb8016c7d444da66bd7e1e242c8e2
出典データセット
uspto-grants-1979_11
特許番号
US04176116

反応ノート

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