2-Amino-2-phenylethan-1-ol → (R)-N2-(Boc)-N5-(Cbz)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amide

HRID 366052ノート

反応式

HRID 366052 の反応式
[N+](C1C=CC=CC=1O[C:11](=[O:35])[C@@H:12]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O-])=O.[CH:36]1[CH:41]=[CH:40][C:39]([C@H:42]([NH2:45])[CH2:43][OH:44])=[CH:38][CH:37]=1>C(Cl)Cl>[C:14]([NH:13][C@H:12]([C:11]([NH:45][C@H:42]([C:39]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1)[CH2:43][OH:44])=[O:35])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

参加物

4

反応物 2

HCID 1347972-Amino-2-phenylethan-1-olHCID 54461433Nalpha-Boc-Ndelta-Cbz-(R)-ornithine o-nitrophenyl ester

生成物 1

HCID 131722056(R)-N2-(Boc)-N5-(Cbz)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amide収率 84.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Prepared according to the method described in Example 4(b) above from Nα -Boc-Nδ -Cbz-(R)-ornithine o-nitrophenyl ester (4.0 g; 9.22 mmol; see Example 4(a) above) and (S)-(+)-phenylglycinol (1.26 g; 9.22 mmol; 1 eq.) and CH2Cl2 (160 mL). The reaction mixture was stirred overnight and then washed with saturated aqueous KHSO4, saturated aqueous Na2CO3, brine, dried with Na2SO4, filtered and concentrated to dryness. The residue was triturated with ether to obtain 3.8 g of the sub-title compound as a white solid.

後処理

  1. customPrepared
  2. washwashed with saturated aqueous KHSO4, saturated aqueous Na2CO3, brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-8cd4c887def642c489315ee6a3322969
出典データセット
uspto-grants-2000_10
特許番号
US06127414

反応ノート

読み込み中…