Benzaldehyde → HCID 101104055、化合物

HRID 1067100

反応式

HRID 1067100 の反応式
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+]>O.CO>[CH2:19]([NH:13][C@H:12]([C:14]([OH:16])=[O:15])[CH2:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

7

反応物 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 6993436(2S)-2-amino-5-(((tert-butoxy)carbonyl)amino)pentanoic acid

生成物 1

HCID 101104055HCID 101104055、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of Nδ-Boc-ornithine (7.0 g), 2M sodium hydroxide (20 ml), benzaldehyde (3.2 ml) and methanol (10 ml) was cooled to 0° C. and sodium borohydride (2.7 g) was added. After 1 hr at 0° C., the mixture was kept at 25° C. for 12 h. Water (100 ml) was added and the mixture extracted with ether (2×60 ml). The combined organic extract was washed with sat. sodium bicarbonate (ca. 150 ml) and water, and dried over anhydrous sodium sulfate. After concentration in vacuo, the desired product (4.5 g) was obtained as a white solid: 1H NMR (400 MHz, CD3OD) δ1.42 (s, 9H), 1.60 (m, 2H), 1.84 (m, 2H), 3.03 (m, 2H), 3.50 (t, J=7.4 Hz, 1H), 4.11 (d, J=11.9 Hz, 1H), 4.21 (d, J=11.9 Hz, 1H), 7.41 (m, 3H), and 7.49 (m, 2H).

後処理

  1. waitthe mixture was kept at 25° C. for 12 h
  2. extractionthe mixture extracted with ether (2×60 ml)
  3. extractionThe combined organic extract
  4. washwas washed with sat. sodium bicarbonate (ca. 150 ml) and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration in vacuo

出典と根拠

ORDレコード
ord-4a3a99e99369426c9f31187f82c89fa7
出典データセット
uspto-grants-2001_06
特許番号
US06245746B1

関連ノート

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