Triethylamine → [(4-Benzyloxy-1-methoxymethyl-isoquinoline-3-carbonyl)-amino]-acetic acid benzyl ester

HRID 250449ノート

反応式

HRID 250449 の反応式
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][O:20][CH3:21])=[N:11][C:10]=1[C:22](O)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.ClC(OCC(C)C)=O.Cl.[CH2:41]([O:48][C:49](=[O:52])[CH2:50][NH2:51])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(Cl)Cl>[CH2:41]([O:48][C:49](=[O:52])[CH2:50][NH:51][C:22]([C:10]1[N:11]=[C:12]([CH2:19][O:20][CH3:21])[C:13]2[C:18]([C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:23])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 11701227Benzyl 2-aminoacetate hydrochlorideHCID 667128924-Benzyloxy-1-methoxymethyl-isoquinoline-3-carboxylic acid

生成物 1

HCID 66712976[(4-Benzyloxy-1-methoxymethyl-isoquinoline-3-carbonyl)-amino]-acetic acid benzyl ester収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 4-benzyloxy-1-methoxymethyl-isoquinoline-3-carboxylic acid (120 mg, 0.37 mmol), NEt3 (109 μl, 0.78 mmol), and CH2Cl2 (7 ml) cooled with an ice bath was added ClCO2iBu (52 μl, 0.39 mmol) with stirring. After stirring for 15 min glycine benzyl ester hydrochloride (79 mg, 0.39 mmol) was added and the mixture was stirred for another 15 min before the ice bath was removed. Stirring was then continued at ambient temperature for additional 1.5 h. Subsequently the mixture was concentrated in vacuo. To the residue was added water (10 ml) and a few drops of aqueous 6N HCl. The mixture was extracted with EtOAc (15 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give a yellowish gum. Purification by flash column chromatography on silica gel using hexanes:EtOAc=7:3 as the eluent gave the title compound as a yellow oil (141 mg); MS-(+)-ion: M+1=471.1.

後処理

  1. temperaturecooled with an ice bath
  2. additionwas added
  3. customwas removed
  4. stirringStirring
  5. concentrationSubsequently the mixture was concentrated in vacuo
  6. additionTo the residue was added water (10 ml) and a few drops of aqueous 6N HCl
  7. extractionThe mixture was extracted with EtOAc (15 ml)
  8. dry with materialThe organic phase was dried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give a yellowish gum
  11. customPurification by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-995966a9b5ce498fbc77584cf0f3a136
出典データセット
uspto-grants-2011_01
特許番号
US07863292B2

反応ノート

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