2-Hydroxy-2-[(1H-indol-3-yl)methyl]-4-(methoxyimino)pentanedioic acid → D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-

HRID 252665ノート

反応式

HRID 252665 の反応式
[OH:1][C:2]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)([C:11]([OH:13])=[O:12])[CH2:3][C:4](=[N:8]OC)[C:5]([OH:7])=[O:6].[H][H]>N.[C].[Rh]>[OH:1][C@@:2]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)([C:11]([OH:13])=[O:12])[CH2:3][C@@H:4]([NH2:8])[C:5]([OH:7])=[O:6].[OH:1][C@:2]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)([C:11]([OH:13])=[O:12])[CH2:3][C@@H:4]([NH2:8])[C:5]([OH:7])=[O:6]

参加物

6

反応物 2

HCID 714413032-Hydroxy-2-[(1H-indol-3-yl)methyl]-4-(methoxyimino)pentanedioic acidHCID 178418361HCID 178418361、化合物

生成物 2

HCID 9814579D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-HCID 9922096D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4R)-

試薬・触媒・溶媒 2

HCID 178503043HCID 178503043、化合物触媒HCID 222Ammonia溶媒

実験手順

0.264 g (0.824 mmol) of 4-hydroxy-4-(3-indolylmethyl)-2-methoxyiminoglutaric acid was dissolved in 10 ml of aqueous 28% ammonia. 0.18 g of 5% rhodium carbon (dry product) was added and the mixture stirred at a hydrogen pressure of 7.5 atmospheres for 18 hours. The catalyst was filtered off and the solvent was distilled off under reduced pressure, to obtain the residue. The resulting residue was analyzed by NMR, and a mixture of 0.115 g (0.395 mmol; yield, 48%) of (2S, 4S)/(2R, 4R)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (monatin) and 0.065 g (0.223 mmol; yield, 27%) of (2S, 4R)/(2R, 4S)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid was found to have been generated.

後処理

  1. filtrationThe catalyst was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. customto obtain the residue

出典と根拠

ORDレコード
ord-cb18537b5e1f4bdf8a323aee0371b1a5
出典データセット
uspto-grants-2011_01
特許番号
US07868187B2

反応ノート

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