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

HRID 719107Notes

Reaction equation

HRID 719107 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1dbe34b198a047cca45bd686007c8a7d
Source dataset
uspto-grants-2006_11
Patent number
US07132416B2

Reaction notes

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