Hydrochloric Acid → 2-(N-benzyloxycarbonyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid

HRID 1590804ノート

反応式

HRID 1590804 の反応式
ClC(OCC(C)C)=O.[CH2:9]([O:16][C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=O)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN1CCOCC1.[CH3:34][C:35]1[C:40]([C:41]([OH:43])=[O:42])=[C:39]([NH:44][C:45](=[O:51])[C@H:46]([CH:48]([CH3:50])[CH3:49])[NH2:47])[CH:38]=[CH:37][CH:36]=1.Cl>C(OCC)(=O)C.CN(C)C=O.O1CCCC1>[CH2:9]([O:16][C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([NH:47][C@H:46]([C:45]([NH:44][C:39]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:34])[C:40]=1[C:41]([OH:43])=[O:42])=[O:51])[CH:48]([CH3:50])[CH3:49])=[O:23])=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2 回HCID 62365Isobutyl chloroformateHCID 101987Benzyloxycarbonyl-L-prolineHCID 541805686-methyl-2-(L-valylamino)benzoic acid

生成物 1

HCID 537310482-(N-benzyloxycarbonyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid収率 73.9%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Isobutyl chloroformate (0.1 ml) was added dropwise to a tetrahydrofuran solution (2.5 ml) containing N-benzyloxycarbonyl-L-proline (229 mg) and N-methylmorpholine (0.1 ml) at -12° C. to -18° C., and the mixture was stirred at this temperature for nine minutes. An N,N-dimethylformamide solution (1.5 ml) containing 6-methyl-2-(L-valylamino)benzoic acid (142 mg) and N-methylmorpholine (0.075 ml) was added dropwise to the above solution at -15° C., and the resultant solution was stirred at this temperature for 20 minutes and then at room temperature for 45 minutes. Thereafter, 1N hydrochloric acid was added to stop the reaction, and extraction was performed using ethyl acetate. The organic layer was successively washed with 1N hydrochloric acid and brine, dried over sodium sulfate, and concentrated. The residue was purified by flash column chromatography using silica gel to obtain 202 mg of 2-(N-benzyloxycarbonyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid.

後処理

  1. additionwas added dropwise to the above solution at -15° C.
  2. waitat room temperature for 45 minutes
  3. customthe reaction, and extraction
  4. washThe organic layer was successively washed with 1N hydrochloric acid and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-8f66ab7ea13f45ce9a92f01169b0ab9f
出典データセット
uspto-grants-1993_04
特許番号
US05204462

反応ノート

読み込み中…