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Cornforth reagent → (3S,6R)-4-(tert-butoxycarbonyl)-6-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-3-carboxylic acid

HRID 629700
ノート
印刷プレビュー

反応式

HRID 629700 の反応式
[OH:1][CH2:2][C@H:3]1[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][C@@H:6]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH:24][C:25](=[O:45])[C@H:26]([CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[NH:27][C:28]([O:30][CH3:31])=[O:29])[O:5][CH2:4]1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-:58][Cr](O[Cr]([O-])(=O)=O)(=O)=O>CN(C=O)C>[C:12]([O:11][C:9]([N:8]1[CH2:7][C@@H:6]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH:24][C:25](=[O:45])[C@H:26]([CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[NH:27][C:28]([O:30][CH3:31])=[O:29])[O:5][CH2:4][C@H:3]1[C:2]([OH:58])=[O:1])=[O:10])([CH3:14])([CH3:15])[CH3:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2724130Cornforth reagentHCID 86726307(2R,5R)-5-hydroxymethyl-2-{2-[2-((S)-2-methoxycarbonylamino-3,3-diphenyl-propionylamino)-phenyl]-ethyl}-morpholine-4-carboxylic acid tert-butyl ester

生成物 1

HCID 86726308(3S,6R)-4-(tert-butoxycarbonyl)-6-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

To tert-butyl (2R,5R)-5-(hydroxymethyl)-2-[2-(2-{[N-(methoxycarbonyl)-β-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate (1 eq) in DMF (0.1M) at rt were added PDC (10 eq) and 4A molecular sieve (1 g/mmol of substrate). The reaction mixture was stirred at rt for 16 hrs. The reaction mixture was then filtered on a celite and the celite pad was washed with EtOAc and water. The filtrate was extracted with EtOAc. The combined organic layers were washed with brine, 1N aqueous HCl and brine, dried over Na2SO4, filtered and concentrated. The crude product was used as such for next step.

後処理

  1. filtrationThe reaction mixture was then filtered on a celite
  2. washthe celite pad was washed with EtOAc and water
  3. extractionThe filtrate was extracted with EtOAc
  4. washThe combined organic layers were washed with brine, 1N aqueous HCl and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-306cf645861a4f429b86a208025f74df
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09315475B2

反応ノート

読み込み中…

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