Potassium Carbonate → Methyl 3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-benzyloxyphenyl)-6-methylbenzoate

HRID 2247426Notes

Reaction equation

HRID 2247426 reaction equation
[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][C:10]=1[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:34]1[CH:35]=[C:36]([C:41]([CH3:44])=[CH:42][CH:43]=1)[C:37]([O:39][CH3:40])=[O:38].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[C:15]([O:14][C:13]([NH:12][CH2:11][C:10]1[CH:20]=[C:21]([C:34]2[CH:35]=[C:36]([C:41]([CH3:44])=[CH:42][CH:43]=2)[C:37]([O:39][CH3:40])=[O:38])[CH:22]=[CH:23][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:19])([CH3:16])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 316201Methyl 5-bromo-2-methylbenzoateHCID 59219302HCID 59219302, compound

Product 1

HCID 68633850Methyl 3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-benzyloxyphenyl)-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.01 g of t-butyl N-[2-benzyloxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]carbamate, 593 mg of methyl 3-bromo-6-methylbenzoate, 130 mg of dichloro-bistriphenyl phosphinoferrocene palladium and 1 g of potassium carbonate were dissolved in 15 ml of dimethoxyethane, and the mixture was heated under reflux for 4 hours in a nitrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was evaporated. The residue was purified by silica gel column, to give methyl 3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-benzyloxyphenyl)-6-methylbenzoate in the 4:1 hexane-ethyl acetate fraction. This crude product was dissolved in 100 ml of methanol, then 500 mg of 10% Pd—C was added thereto, and the mixture was stirred overnight at room temperature in a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated. The residue was purified by silica gel column, to give 521 mg of the title compound in the 5:1 hexane-ethyl acetate fraction.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours in a nitrogen atmosphere
  3. filtrationThe reaction mixture was filtered through Celite
  4. customthe filtrate was evaporated
  5. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-159dd910de034789b835a9b190454a22
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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