Benzyl 6-[(tert-butoxycarbonyl)amino]-2-methyl-3-vinylbenzoate → 6-[(Tert-butoxycarbonyl)amino]-3-ethyl-2-methylbenzoic acid

HRID 1725913Notes

Reaction equation

HRID 1725913 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[C:13]([CH3:25])[C:12]([CH:26]=[CH2:27])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[OH-].[Pd+2].[OH-].CO>[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH3:25])[C:12]([CH2:26][CH3:27])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 68862949Benzyl 6-[(tert-butoxycarbonyl)amino]-2-methyl-3-vinylbenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 688658416-[(Tert-butoxycarbonyl)amino]-3-ethyl-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of Example 145A (450 mg, 1.2 mmol), palladium hydroxide (540 mg), and methanol (150 mL) was heated to 50° C. in a Paar shaker under 65 psi hydrogen pressure for 72 hours. The mixture was filtered, concentrated, and purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/0.1% aqueous TFA over 8 minutes (10 minute run time) at a flow rate of 40 mL/min to provide the desired product. MS (ESI(+)) m/e 280 (M+H)+, 297 (M+NH4)+, 302 (M+Na)+; (ESI(−)) m/e 278 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 13.28 (br s, 1H), 8.35 (s, 1H), 7.32 (d, 1H), 7.17 (d, 1H), 2.58 (q, 2H), 2.24 (s, 3H), 1.43 (s, 9H), 1.12 (t, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)
  4. customover 8 minutes
  5. custom(10 minute run time)

Sources & evidence

ORD record
ord-da0f4f8a24d5429c86d5f696c86ad073
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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