Methanol → 2-(S)-Hydroxy-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid

HRID 1480933노트

반응식

HRID 1480933 반응식
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[OH:23][C@@H:24]([CH2:28][NH2:29])[C:25]([OH:27])=[O:26].CO>C[O-].[Na+]>[OH:23][C@@H:24]([CH2:28][NH:29][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH:9]=2)=[O:4])[C:25]([OH:27])=[O:26]

참가 물질

5

반응물 3

HCID 887MethanolHCID 6999797L-IsoserineHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

생성물 1

HCID 717351402-(S)-Hydroxy-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid수율 93.5%

시약·촉매·용매 1

HCID 10942334Sodium Methoxide용매

실험 절차

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (90 mg, 0.31 mmol) and 2-(S)-hydroxy-3-amino-propionic acid (Sigma-Aldrich) (96 mg, 0.92 mmol) in 0.5 N NaOMe in MeOH solution (1.22 mL, 0.61 mmol) was microwaved at 120° C. for 1 h and concentrated. Residue was dissolved in water (70 mL) and acidified by 1 N HCl solution to pH=3-4. It was extracted with EtOAc, Organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give the title compound (105 mg, 0.29 mmol) in 92% yield. LC-MS ESI−: 366.99 (M−1)−.

후처리

  1. customwas microwaved at 120° C. for 1 h
  2. concentrationconcentrated
  3. dissolutionResidue was dissolved in water (70 mL)
  4. extractionIt was extracted with EtOAc, Organic layer
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-316329ae4d7643ca975d302c89961bdf
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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