Methanol → (alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid

HRID 388883Notes

Reaction equation

HRID 388883 reaction equation
CN1CC[N:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]([O:11]CC2C=CC=CC=2)=[O:10])[CH2:4]C1.[H][H].C1(C[C:34](O)=[O:35])C=CC=CC=1.C[OH:38]>[Pd]>[CH3:34][O:35][C:4]([NH:5][C@H:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]([OH:11])=[O:10])=[O:38]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 999Phenylacetic AcidHCID 66648860Benzyl 2-(4-methylpiperazin-1-yl)-2-phenylacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A methanol (10 mL) solution of either stereoisomer of benzyl 2-(4-methylpiperazin-1-yl)-2-phenylacetate (1.0 g, 3.1 mmol) was added to a suspension of 10% Pd/C (120 mg) in methanol (5.0 mL). The reaction mixture was exposed to a balloon of hydrogen, under a careful monitoring, for <50 minutes. Immediately after the completion of the reaction, the catalyst was filtered through diatomaceous earth (CELITE®) and the filtrate was concentrated in vacuo to provide Cap-7, contaminated with phenylacetic acid as a tan foam (867.6 mg; mass is above the theoretical yield). The product was used for the next step without further purification. 1H NMR (DMSO-d6, δ=2.5, 500 MHz) δ 7.44-7.37 (m, 2H), 7.37-7.24 (m, 3H), 3.92 (s, 1H), 2.63-2.48 (app. br s, 2H), 2.48-2.32 (m, 6H), 2.19 (s, 3H); RT=0.31 (Condition II); >90% homogeneity index; LC-MS: Anal. Calcd. for [M+H]+ C13H19N2O2: 235.14. found 235.15; HRMS: Anal. Calcd. for [M+H]+ C13H16N2O2: 235.1447. found 235.1440.

Workup

  1. customImmediately after the completion of the reaction
  2. filtrationthe catalyst was filtered through diatomaceous earth (CELITE®)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto provide Cap-7
  5. customtheoretical yield)
  6. customThe product was used for the next step without further purification
  7. customRT=0.31 (Condition II)

Sources & evidence

ORD record
ord-0fe3639181264c398a635690a8654a73
Source dataset
uspto-grants-2013_02
Patent number
US08377980B2

Reaction notes

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