D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)- → 4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid

HRID 252664노트

반응식

HRID 252664 반응식
[NH4+].[OH:2][C:3]([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]([O-:13])=[O:12])[CH2:4][C:5](=[N:9]O)[C:6]([O-:8])=[O:7].[NH4+].[H][H].O[C@@](CC1C2C(=CC=CC=2)NC=1)(C(O)=O)C[C@@H](N)C(O)=O.O[C@](CC1C2C(=CC=CC=2)NC=1)(C(O)=O)C[C@@H](N)C(O)=O>N.[C].[Rh]>[OH:2][C:3]([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])[CH2:4][CH:5]([NH2:9])[C:6]([OH:8])=[O:7]

참가 물질

7

반응물 4

HCID 9814579D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-HCID 9922096D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4R)-HCID 178418361HCID 178418361, 화합물HCID 1785254994-Hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutarate ammonium salt

생성물 1

HCID 99260664-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid

시약·촉매·용매 2

HCID 178503043HCID 178503043, 화합물촉매HCID 222Ammonia용매

실험 절차

0.13 g (0.38 mmol) of 4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutaric acid ammonium salt was dissolved in 5 ml of aqueous 28% ammonia, to which 0.09 g of 5% rhodium carbon was added, for reaction at ambient temperature and a hydrogen pressure of 7.5 atmospheres. 14 hours later, the catalyst was filtered off, and the resulting solution was concentrated to dryness, to obtain a mixture of 0.075 g (0.23 mmol) of the ammonium salt of (2S, 4S)/(2R, 4R)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (monatin) and 0.036 g (0.11 mmol) of the ammonium salt of (2S, 4R)/(2R, 4S)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (monatin).

후처리

  1. additionwas added, for reaction at ambient temperature
  2. filtration14 hours later, the catalyst was filtered off
  3. concentrationthe resulting solution was concentrated to dryness
  4. customto obtain

출처 및 근거

ORD 기록
ord-b28157121a254f509f60977932910e59
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868187B2

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