Anisole → D-Cysteinyl-L-proline acetate

HRID 65857ノート

反応式

HRID 65857 の反応式
C([O:5][C:6](=[O:34])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:33])[C@@H:13]([CH2:22][S:23]CC1C=CC(OC)=CC=1)[NH:14]C(OC(C)(C)C)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)S(O)(=O)=O>ClCCl>[C:6]([OH:34])(=[O:5])[CH3:7].[NH2:14][C@@H:13]([C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:34])=[O:5])=[O:33])[CH2:22][SH:23]

参加物

5

反応物 3

HCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acidHCID 22805345N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteinyl-L-proline tert-butyl ester

生成物 1

HCID 86736006D-Cysteinyl-L-proline acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteinyl-L-proline tert-butyl ester (1.8 g) and anisole (4.4 ml) in dichloromethane (8 ml) chilled in an ice bath, trifluoromethane sulfonic acid (6.0 g) is added. The ice bath is removed and the mixture is stirred at room temperature for 30 minutes. The dichloromethane is removed in vacuo and the residue is triturated with hexane (2 × 200 ml). The residue is dissolved in water and extracted twice with ether. The aqueous phase is applied to a column of 200 ml of cation exchange resin [Dowex 50] in the hydrogen cycle. The column is washed with water until no more acidic material is eluted. The D-cysteinyl-L-proline acetate is eluted with a pyridine-acetic acid buffer pH 6.5, yield 0.66 g. Rf =0.38 (silica gel, chloroform:methanol:acetic acid:water).

後処理

  1. customThe ice bath is removed
  2. customThe dichloromethane is removed in vacuo
  3. customthe residue is triturated with hexane (2 × 200 ml)
  4. dissolutionThe residue is dissolved in water
  5. extractionextracted twice with ether
  6. washThe column is washed with water until no more acidic material
  7. washis eluted
  8. washThe D-cysteinyl-L-proline acetate is eluted with a pyridine-acetic acid buffer pH 6.5, yield 0.66 g

出典と根拠

ORDレコード
ord-44de1137dfff453ab240b0ff57330220
出典データセット
uspto-grants-1978_12
特許番号
US04129571

反応ノート

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