Sodium Carbonate → Methyl 3-phthalimido-3-(3-ethoxy-4-methoxyphenyl)propionate

HRID 1940090노트

반응식

HRID 1940090 반응식
Cl.[NH2:2][CH:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][CH3:19])[CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]2[C:32]1=[O:41])(OCC)=O>O.C(#N)C>[C:32]1(=[O:41])[N:2]([CH:3]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][CH3:19])[CH:10]=2)[CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]12

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 21250974Methyl 3-amino-3-(3-ethoxy-4-methoxyphenyl)propionate hydrochloride

생성물 1

HCID 9821373Methyl 3-phthalimido-3-(3-ethoxy-4-methoxyphenyl)propionate수율 87%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of methyl 3-amino-3-(3-ethoxy-4-methoxyphenyl)propionate hydrochloride (0.87 g, 3.0 mmol) and sodium carbonate (0.32 g, 3.0 mmol) in a mixture of water (10 mL) and acetonitrile (10 mL) was added N-carbethoxyphthalimide (0.68 g, 3.0 mmol). The resulting solution was stirred for 3 hours at room temperature. The acetonitrile was removed in vacuo. To the resulting mixture was added ether (5 mL) and the mixture was stirred at room temperature overnight allowing the ether to evaporate. The resulting white solid was filtered. The solid was washed with water, air dried, and dried in vacuo (60° C., <1 mm) to afford 1.0 g (87%) of methyl 3-phthalimido-3-(3-ethoxy-4-methoxyphenyl)propionate as a white solid: mp 86°-87° C.; 1H NMR (CDCl3) δ7.86-7.63 (m, 4H), 7.16-7.05 (m, 2H), 6.88-6.76 (m, 1H), 5.77 (dd, J=5.9, 10 Hz, 1H), 4.11 (q, J=7 Hz, 2H), 3.84 (s, 3H), 3.77 (dd, J=10, 6.7 Hz, 1H), 3.63 (s, 3,25 (dd, J=5.9, 165.5 Hz, 1H), 1.45 (t, J=7 Hz, 3H); 13C NMR (CDCl3) δ171.0, 168.0, 149.0, 148.2, 133.9, 131.7, 130.9, 123.2, 120.2, 112.5, 111.1, 64.3, 55.8, 51.8, 50.7, 35.8, 14.6; HPLC (Waters Nova-Pak C18 column, 3.9×150 mm, 4 micron, 1 mL/min, 240 nm, 45/55, acetonitrile/0.1% aqueous phosphoric acid 6 min, 100%, Anal. Calcd. for C21H21NO6. Theoretical: C, 65.79; H, 5.52; N, 3.65. Found: C, 65.71; H, 5.70; N, 3.63.

후처리

  1. customThe acetonitrile was removed in vacuo
  2. additionTo the resulting mixture was added ether (5 mL)
  3. stirringthe mixture was stirred at room temperature overnight
  4. customto evaporate
  5. filtrationThe resulting white solid was filtered
  6. washThe solid was washed with water, air
  7. customdried
  8. customdried in vacuo (60° C., <1 mm)

출처 및 근거

ORD 기록
ord-c90fdd321482458abbbc3a1a2c7e2998
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05698579

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