Triethylamine → Methyl N-(4-nitrobenzoyl)-3-amino-3-(3,4-dimethoxyphenyl)propionate

HRID 2392730Notes

Reaction equation

HRID 2392730 reaction equation
Cl.[NH2:2][CH:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[N+:26]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)([O-:28])=[O:27]>O1CCCC1>[N+:26]([C:29]1[CH:30]=[CH:31][C:32]([C:33]([NH:2][CH:3]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=2)[CH2:4][C:5]([O:7][CH3:8])=[O:6])=[O:34])=[CH:36][CH:37]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 16277031Methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride

Product 1

HCID 15547131Methyl N-(4-nitrobenzoyl)-3-amino-3-(3,4-dimethoxyphenyl)propionateYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice bath cooled stirred suspension of methyl 3-amino-3-(3,4-dimethoxyphenyl)propionate hydrochloride(1.38 grams, 5.00 mmol) and triethylamine (1.5 milliliters, 10.8 mmol) in 25 milliliters of tetrahydrofuran was added 4-nitrobenzoyl chloride (0.928 grams, 5.00 mmol) in a single portion. After 15 minutes, the cooling bath was removed and the reaction mixture stirred for 45 minutes. The reaction mixture was then diluted with 50 milliliters of water. The reaction slurry was filtered and the solid washed with water, air-dried, and then dried in vacuo (60 C, <1 mm) to afford 1.86 grams (94%) of the product as a yellow powder: 1H NMR (CDCl3 /TMS, 250 MHz) δ 8.27 (d, J=8.8 Hz, 2 H), 7.98 (d, J=8.8 Hz, 2 H), 7.77 (d, J=8.1 Hz, 1 H, NH), 6.95-6.75 (m, 3 H, Ar), 5.55 (m, 1 H, CH), 3.86 & 3.85 (2 s, 6 H, 2 OCH3), 3.68 (s, 3 H, CO2 CH3), 3.00 (m, 2 H, CH2); 13C NMR (CDCl3 /TMS) δ 172.2, 164.4, 149.6, 1491, 148.7, 139.7, 132.6, 128.2, 123.8, 118.1, 111.2, 109.9, 55.9, 55.8, 52.0, 50.0, 39.3.

Workup

  1. temperatureTo an ice bath cooled
  2. customthe cooling bath was removed
  3. stirringthe reaction mixture stirred for 45 minutes
  4. additionThe reaction mixture was then diluted with 50 milliliters of water
  5. filtrationThe reaction slurry was filtered
  6. washthe solid washed with water
  7. customair-dried
  8. customdried in vacuo (60 C, <1 mm)

Sources & evidence

ORD record
ord-a9847ade3e4f47d7948c128f20cce956
Source dataset
uspto-grants-1998_09
Patent number
US05801195

Reaction notes

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