Benzyl Chloride → HCID 86643598, compound

HRID 2381031Notes

Reaction equation

HRID 2381031 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:21]C(OCC2C=CC=CC=2)=O)[C:17]([O:19][CH3:20])=[O:18])=[CH:11][C:10]=1[O:32][C:33]([N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:34])C1C=CC=CC=1.C([Cl:47])C1C=CC=CC=1>CO.[C].[Pd]>[Cl-:47].[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH3+:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:11][C:10]=1[O:32][C:33]([N:35]1[CH2:36][CH2:37][CH2:38][CH2:39]1)=[O:34]

Participants

5

Reactant 2

HCID 7503Benzyl ChlorideHCID 68722905HCID 68722905, compound

Product 1

HCID 86643598HCID 86643598, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Pyrrolidine-1-carboxylic acid 2-benzyloxy-5-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-phenyl ester (364 mg) was dissolved in methanol (15 ml) containing benzyl chloride (95 mg) and 5% palladium-carbon (50 mg). The mixture was stirred for 3 hours under an atmosphere of hydrogen gas. The catalyst was removed by filtration and washed with methanol. Evaporation of the filtrate gave a gum which was crystallised by trituration with ether. (S)-2-[4-Hydroxy-3-(pyrrolidine-1-carbonyloxy)-phenyl]-1-methoxycarbonyl-ethyl-ammonium chloride was obtained as a white solid, 212 mg; NMR (500 MHz, d6 DMSO) 1.82-1.92 (4H, m), 2.97 (1H, dd J 14, 7), 3.05 (1H, dd J 14, 6), 3.31 (2H, t J 7), 3.49 (2H, t J 7), 3.67 (3H, s), 4.19 (1H, t J ca 6), 6.85-6.88 (3H, m), 8.54 (3H, br s exch D2O), 9.54 (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. customEvaporation of the filtrate
  4. customgave a gum which
  5. customwas crystallised by trituration with ether

Sources & evidence

ORD record
ord-33ebe5c007af4b62983e1bc847aaee70
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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