3,3,5-Trimethylcyclohexanol → 3,3,5-Trimethylcyclohexyl N-benzyloxycarbonyl-L-pyroglutamate

HRID 654835ノート

反応式

HRID 654835 の反応式
[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[CH3:29][C:30]1([CH3:38])[CH2:35][CH:34]([CH3:36])[CH2:33][CH:32](O)[CH2:31]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([O:19][CH:32]1[CH2:33][CH:34]([CH3:36])[CH2:35][C:30]([CH3:38])([CH3:29])[CH2:31]1)=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 82983,3,5-TrimethylcyclohexanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

生成物 1

HCID 228451423,3,5-Trimethylcyclohexyl N-benzyloxycarbonyl-L-pyroglutamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

34.2 g (0.13 mol) of N-benzyloxycarbonyl-L-pyroglutamic acid (prepared according to Berichte 97, 2434 [1964] or Annalen 649, 183 [1961] ) are added to 150 ml of dimethylformamide, followed by 2 g of dimethylaminopyridine and then 18.48 g (0.13 mol) of 3,3,5-trimethylcyclohexanol (mixture of 90% trans isomer and 10% cis isomer) diluted in 50 ml of dimethylformamide. 26.8 g (0.13 mol) of dicyclohexylcarbodiimide are then run in over a period of about 15 minutes, the reaction medium being kept at +5° C. The mixture is then stirred at room temperature for 24 hours, after which the solvent is evaporated off, the residue is taken up with dilute hydrochloric acid and extraction is carried out with chloroform.

後処理

  1. customare then run in over a period of about 15 minutes
  2. custombeing kept at +5° C
  3. customafter which the solvent is evaporated off
  4. extractionthe residue is taken up with dilute hydrochloric acid and extraction

出典と根拠

ORDレコード
ord-66651c66750d4be383bc594105b77fa0
出典データセット
uspto-grants-1992_07
特許番号
US05134157

反応ノート

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