Triethylamine → 3-(2-tert-Butoxycarbonylamino-2-methylpropyl)benzoic acid methyl ester

HRID 1866508Notes

Reaction equation

HRID 1866508 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]([CH3:18])([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C]=O>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:5][C:6](=[O:19])[C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:19])([CH3:18])[CH3:17])[CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 58907464tert-butyl N-[1-(3-bromophenyl)-2-methylpropan-2-yl]carbamateHCID 178418416HCID 178418416, compound

Product 1

HCID 597135613-(2-tert-Butoxycarbonylamino-2-methylpropyl)benzoic acid methyl esterYield 116.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent

Procedure

A solution of [2-(3-bromophenyl)-1,1-dimethylethyl]carbamic acid tert-butyl ester (Preparation 32) (7.0 g, 21 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.74 g, 2.1 mmol) and triethylamine (5.94 ml, 43 mmol) in methanol (250 ml) was heated to 100° C. under 100 psi carbon monoxide for 12 hours. The reaction mixture was filtered through arbocel and the filtrate concentrated in vacuo and purified by flash column chromatography on silica gel eluting with dichloromethane:pentane (50:50 by volume) to afford the title compound as a yellow solid (3.76 g). 1H NMR (400 MHz, CDCl3) δ=7.92-7.90 (1H, m), 7.82 (1H, s), 7.35-7.34 (2H, m), 4.24 (1H, bs), 3.90 (3H, s), 3.05 (2H, s), 1.48 (9H, s), 1.26 (6H, s). LRMS (electrospray) m/z 208 [M+H−BOC]+

Workup

  1. filtrationThe reaction mixture was filtered through arbocel
  2. concentrationthe filtrate concentrated in vacuo
  3. custompurified by flash column chromatography on silica gel eluting with dichloromethane:pentane (50:50 by volume)

Sources & evidence

ORD record
ord-df2fb9691c814956ac4f62187dde65ab
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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