Water → Methyl N-(3-methoxybenzoyl)-3-amino-3-(3',4'-dimethoxyphenyl)propionate

HRID 1003604Notes

Reaction equation

HRID 1003604 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.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](Cl)=[O:32].O>O1CCCC1>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([NH: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])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 16277031Methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride

Product 1

HCID 18797724Methyl N-(3-methoxybenzoyl)-3-amino-3-(3',4'-dimethoxyphenyl)propionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice bath stirred suspension of methyl 3-amino-3-(3',4'-dimethoxyphenyl)propionate hydrochloride (0.689 grams, 2.50 mmol) and 0.7 milliliters of triethylamine in 20 milliliters of anhydrous tetrahydrofuran was added 3-methoxybenzoyl chloride (2.5 mmol) via syringe. After 30 minutes, the reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was then treated with 20 milliliters of water. The tetrahydrofuran was removed in vacuo and the resulting mixture extracted with methylene chloride (2 times with 25 milliliters). The combined extracts were dried over sodium sulfate and contracted to afford a thick oil. The crude product was purified by flash chromatography (silica gel, 1.4/8.6 ethyl acetate/hexanes) to afford 0.5 grams (56%) as a pale green solid (wax): mp 123.5-125° C.; 1H NMR (CDCl3 /TMS) δ 8.96 (d, J=7.9, 1 H), 8.19 (m, 1 H), 7.45 (m, 1 H), 7.12-6.68 (m, 5 H), 5.59 (m, 1 H), 4.00 (s, 3 H, OCH3), 3.87 (s, 3 H, OCH3), 3.85 (s, 3 H, OCH3), 3.63 (s, 3 H OCH3), 2.96 (m, 2 H, CH2); 13C NMR (CDCl3 /TMS) δ 171.6, 164.4, 157.6, 148.9, 148.2, 133.8, 132.8, 132.3, 121.3, 121.2, 118.1, 111.3, 111.2, 109.9. 55.8, 55.8, 51.6, 49.7, 40.4; TLC (2/8 ehtyl acetate/hexanes, UV) Rf =0.26. Anal. Calcd for C20H23NO6. Theory C, 64.33; H, 6.21; N, 3.75. Found C, 64.31; H, 6.25; N, 3.63.

Workup

  1. stirringstirred for 1 hour
  2. customThe tetrahydrofuran was removed in vacuo
  3. extractionthe resulting mixture extracted with methylene chloride (2 times with 25 milliliters)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customto afford a thick oil
  6. customThe crude product was purified by flash chromatography (silica gel, 1.4/8.6 ethyl acetate/hexanes)
  7. customto afford 0.5 grams (56%) as a pale green solid (wax)

Sources & evidence

ORD record
ord-835a03c1872d43a1badc291ff34fb534
Source dataset
uspto-grants-2000_04
Patent number
US06046221

Reaction notes

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