Benzoic acid, 4-amino-, 1,1-dimethylethyl ester → HCID 68379697, compound

HRID 1410053Notes

Reaction equation

HRID 1410053 reaction equation
[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=O)[O:3]1.[NH2:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:21][CH:20]=1>CC(O)=O.C(Cl)Cl>[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH2:12][NH:18][C:19]2[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[CH:21][CH:20]=2)[O:3]1

Participants

5

Reactant 2

HCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 27605863-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Product 1

HCID 68379697HCID 68379697, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (100 mg, 0.43 mmol), tert-butyl 4-aminobenzoate (83 mg, 0.43 mmol), NaHB(OAc)3 (273 g, 1.29 mmol) and AcOH (2 drops) in 30 mL of DCM was stirred at room temperature overnight. The mixture was washed with sat NaHCO3 (30 mL), water (2×30 mL), and brine (30 mL) dried over Na2SO4 concentrated under reduce pressure to give a crude tert-butyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylamino)benzoate (130 mg) as a black oil. LC-MS: 410 [M+H]+, tR=1.92 min.

Workup

  1. washThe mixture was washed with sat NaHCO3 (30 mL), water (2×30 mL), and brine (30 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c23d7fdbad1449c79814480c965a3ada
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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