Methanesulfonic Acid → (R)-alpha-{N-[(S)-1-(t-Butoxycarbonyl)propyl]carbamoyl}-4-hydroxybenzylamine

HRID 719107ノート

反応式

HRID 719107 の反応式
C(OC([NH:11][C@@H:12]([C:20](=[O:32])[NH:21][C@H:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH3:24])[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=O)C1C=CC=CC=1.CS(O)(=O)=O>C(O)C.[Pd]>[C:28]([O:27][C:25]([C@@H:22]([NH:21][C:20]([C@H:12]([NH2:11])[C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)=[O:32])[CH2:23][CH3:24])=[O:26])([CH3:29])([CH3:30])[CH3:31]

参加物

5

反応物 2

HCID 6395Methanesulfonic AcidHCID 69551129(R)-N-Benzyloxycarbonyl-alpha-{N-[(S)-1-(t-butoxycarbonyl)propyl]carbamoyl}-4-hydroxybenzylamine

生成物 1

HCID 69198528(R)-alpha-{N-[(S)-1-(t-Butoxycarbonyl)propyl]carbamoyl}-4-hydroxybenzylamine

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of (R)-N-Benzyloxycarbonyl-α-{N-[(S)-1-(t-butoxycarbonyl)propyl]carbamoyl}-4-hydroxybenzylamine Method 18; 1.80 g, 4.07 mmol) and Pd/C (0.2 g, 5%) in ethanol (30 ml, 95%) was stirred under hydrogen gas at room temperature for 2 hours. The reaction mixture was filtered through silica gel (2 g) and concentrated. The residue was dissolved in acetone (20 ml) and methanesulphonic acid (0.40 g, 4.16 mmol) was added. No crystallization was obtained and the solvent was removed under reduced pressure. The crude product was purified by preparative HPLC using a gradient of 20–50% MeCN in 0.1M ammonium acetate buffer as eluent. The title compound was obtained in 0.350 g (28%) as a white solid. NMR (400 MHz, DMSO-d6): 0.75 (3H, t), 1.40 (9H, s), 1.50–1.75 (2H, m), 2.70 (1H, s), 4.00–4.10 (1H, m), 4.30 (1H, s), 6.65 (2H, d), 7.15 (2H, d), 8.15 (1H, d).

後処理

  1. filtrationThe reaction mixture was filtered through silica gel (2 g)
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in acetone (20 ml)
  4. customNo crystallization
  5. customwas obtained
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-1dbe34b198a047cca45bd686007c8a7d
出典データセット
uspto-grants-2006_11
特許番号
US07132416B2

反応ノート

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