3-(4-tert-Butoxycarbonylmethoxy-3-chloro-phenyl)-propionic acid benzyl ester → 3-(4-Tert-butoxycarbonylmethoxy-3-chloro-phenyl)-propionic acid

HRID 386717Notes

Reaction equation

HRID 386717 reaction equation
C([O:8][C:9](=[O:28])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:14]([Cl:27])[CH:13]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[C:23]([O:22][C:20]([CH2:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][C:9]([OH:28])=[O:8])=[CH:13][C:14]=1[Cl:27])=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 1

HCID 667975133-(4-tert-Butoxycarbonylmethoxy-3-chloro-phenyl)-propionic acid benzyl ester

Product 1

HCID 667975163-(4-Tert-butoxycarbonylmethoxy-3-chloro-phenyl)-propionic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(4-tert-Butoxycarbonylmethoxy-3-chloro-phenyl)-propionic acid benzyl ester (step 2) (6.35 g, 15.7 mmol) in THF (60 ml) was added to a suspension of palladium on activated carbon (10% wt, 0.84 g, 0.78 mmol) in THF (35 ml) under an inert atmosphere. The resultant mixture was placed under an atmosphere of hydrogen (0.35 bar) for 3 h. The reaction mixture was filtered through Celite® (filter material) and washed through with THF (100 ml). The filtrate was concentrated in vacuo to afford the title compound as a yellow oil; 1H NMR (400 MHz, DMSO-d6) δ 12.15 (1H, s), 7.31 (1H, d), 7.12 (1H, dd), 6.91 (1H, d), 4.74 (2H, s), 2.75 (2H, t), 2.51 (2H, t), 1.38 (9H, s).

Workup

  1. filtrationThe reaction mixture was filtered through Celite® (filter material)
  2. washwashed through with THF (100 ml)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6ea0793eceb84874a6b809b0be8df73b
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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