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

HRID 719107노트

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HRID 719107 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1dbe34b198a047cca45bd686007c8a7d
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132416B2

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