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

HRID 1480933ノート

反応式

HRID 1480933 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 10942334Sodium Methoxide溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-316329ae4d7643ca975d302c89961bdf
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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