Ammonia → N-[(Benzyloxy)carbonyl]-L-isoleucyl-L-prolyl-L-prolinamide

HRID 1282960ノート

反応式

HRID 1282960 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=O)=[O:22])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.[NH3:42]>O1CCCC1.C(N(CC)CC)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:42])=[O:27])=[O:22])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 222AmmoniaHCID 62365Isobutyl chloroformateHCID 54515815N-[(Benzyloxy)carbonyl]-L-isoleucyl-L-prolyl-L-proline

生成物 1

HCID 53756909N-[(Benzyloxy)carbonyl]-L-isoleucyl-L-prolyl-L-prolinamide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

Benzyloxycarbonyl-isoleucyl-prolyl-proline (4.5 g) is dissolved in a mixture of tetrahydrofuran (30 ml) and triethylamine (1.4 ml). The solution is chilled in a -5° cooling bath and isobutyl chloroformate (1.6 ml) is added. The solution is allowed to warm to room temperature (10 minutes) and concentrated aqueous ammonia (10 ml) is added. After four hours stirring at room temperature, the reaction is concentrated in vacuo, diluted with ethyl acetate and washed sequentially with saturated sodium bicarbonate, water, 0.1 N hydrochloric acid and water. The organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo to give the title compound.

後処理

  1. temperatureThe solution is chilled in a -5°
  2. temperaturecooling bath
  3. additionis added
  4. concentrationthe reaction is concentrated in vacuo
  5. additiondiluted with ethyl acetate
  6. washwashed sequentially with saturated sodium bicarbonate, water, 0.1 N hydrochloric acid and water
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated to dryness in vacuo

出典と根拠

ORDレコード
ord-ba999c62b81b408e83dcc33283325721
出典データセット
uspto-grants-1976_08
特許番号
US03973006

反応ノート

読み込み中…