Quinaldic Acid → N-tert.butyl-1-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-cysteinyl]amino]butyl]-2(S)-piperidinecarboxamide

HRID 742902

反応式

HRID 742902 の反応式
[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[CH2:14][C@@H:15]([OH:31])[C@@H:16]([NH:24][C:25](=[O:30])[C@H:26]([CH2:28][SH:29])[NH2:27])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:32](O)(=[O:43])[C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1.OC1C2N=NNC=2C=CC=1.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[CH2:14][C@@H:15]([OH:31])[C@@H:16]([NH:24][C:25](=[O:30])[C@H:26]([CH2:28][SH:29])[NH:27][C:32]([C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1)=[O:43])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 5

HCID 7124Quinaldic AcidHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 86746294N-tert.butyl-1-[3(S)-[(L-cysteinyl)amino]-2(R)-hydroxy-4-phenylbutyl]-2(S)-piperidinecarboxamideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 86746293N-tert.butyl-1-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-cysteinyl]amino]butyl]-2(S)-piperidinecarboxamide収率 41.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 650 mg of N-tert.butyl-1-[3(S)-[(L-cysteinyl)amino]-2(R)-hydroxy-4-phenylbutyl]-2(S)-piperidinecarboxamide and 242 mg of quinaldic acid was cooled in an ice/salt mixture. 189 mg of hydroxybenzotriazole, 161 mg of N-ethylmorpholine and 317 mg of dicyclohexylcarbodiimide were added and the mixture was stirred for 64 hours. The mixture was diluted with ethyl acetate and filtered, and the filtrate was then evaporated. The residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution. The organic phase was washed with sodium chloride solution and then evaporated. The residue was chromatographed on silica gel using dichloromethane/methanol (19:1) for the elution to give 350 mg of N-tert.butyl-1-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-cysteinyl]amino]butyl]-2(S)-piperidinecarboxamide as a white solid; MS: m/e 620 [M+H]+.

後処理

  1. filtrationfiltered
  2. customthe filtrate was then evaporated
  3. customThe residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution
  4. washThe organic phase was washed with sodium chloride solution
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

出典と根拠

ORDレコード
ord-de354d441a9c4033a82cb08566fa0d7b
出典データセット
uspto-grants-1996_09
特許番号
US05554756

関連ノート

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