Benzyl Chloride → HCID 86643599, compound

HRID 2381032Notes

Reaction equation

HRID 2381032 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:25]C(OCC1C=CC=CC=1)=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[C:8]([O:20][C:21](=[O:24])[NH:22][CH3:23])[CH:7]=1.C([Cl:44])C1C=CC=CC=1>CO.[Pd]>[Cl-:44].[OH:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C@H:4]([NH3+:25])[C:3]([O:2][CH3:1])=[O:36])=[CH:7][C:8]=1[O:20][C:21](=[O:24])[NH:22][CH3:23]

Participants

5

Reactant 2

HCID 7503Benzyl ChlorideHCID 68725083HCID 68725083, compound

Product 1

HCID 86643599HCID 86643599, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-3-methylcarbamoyloxy-phenyl)-propionic acid methyl ester (427 mg) was dissolved in methanol (40 ml) containing 5% Pd—C (46 mg) and benzyl chloride (140 mg). The mixture was stirred under an atmosphere of hydrogen for 4 hours. The catalyst was removed by filtration and washed with methanol. The filtrate was evaporated to dryness giving a gum which was triturated with ether. (S)-2-(4-Hydroxy-3-methylcarbamoyloxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride was obtained as a white solid, 239 mg; NMR (500 MHz, d6 DMSO) 2.64 (ca 3H, d J 5), 2.97 (1H, dd J 14.5, 7), 3.04 (1H, dd J 14.5, 6), 3.67 (3H, s), 4.19 (1H, t J 6.5), 6.82-6.88 (3H, m), 7.44 (1H, q J 5 s exch D2O), 8.52 (3H, br s exch D2O), 9.57 (1H, s, exch D2O); HPLC/MS retention time 3.04 min, m/z 309 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. customThe filtrate was evaporated to dryness
  4. customgiving a gum which
  5. customwas triturated with ether

Sources & evidence

ORD record
ord-1dedef5222404df38cff15b42ac2d4bf
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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