Potassium Carbonate → 2,2'-[(2-{[3-(Benzyloxy)-3-oxopropyl]amino}-2-oxoethyl)imino]diacetic acid

HRID 1488254

반응식

HRID 1488254 반응식
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C([O-])([O-])=O.[K+].[K+].[O:21]=[C:22]1[CH2:27][N:26]([CH2:28][C:29]([OH:31])=[O:30])[CH2:25][C:24](=[O:32])[O:23]1>CN(C=O)C>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][CH2:3][NH:2][C:22](=[O:21])[CH2:27][N:26]([CH2:25][C:24]([OH:32])=[O:23])[CH2:28][C:29]([OH:31])=[O:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1695312,6-dioxo-N-(carboxymethyl)morpholineHCID 19434764Benzyl 3-aminopropanoate hydrochloride

생성물 1

HCID 1179963602,2'-[(2-{[3-(Benzyloxy)-3-oxopropyl]amino}-2-oxoethyl)imino]diacetic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To an ice bath cooled solution of benzyl 3-aminopropanoate hydrochloride (4.49 g, 20.8 mmol) in DMF (30 mL) was added K2CO3 (3.02 g, 21.84 mmol) and the resulting mixture was stirred at o° C. for 2 hr. The mixture was then filtered and the filtrate was added to an ice bath cooled solution of 2-(2,6-dioxomorpholino)acetic acid (4.47 g, 25.8 mmol) in DMF (30 mL). The resulting mixture was stirred at 0° C. for 30 min, then at rt for 2 hr. The reaction was quenched by the addition of water (30 mL) and the resulting mixture was concentrated. The residue was stirred with water (40 mL), and the resulting precipitate was collected through filtration and dried to give the title compound. 1H NMR (DMSO-d6) δ 2.53 (t, J=6.8, 2H), 3.27 (s, 2H), 3.36 (q, J=6.2, 2H), 3.42 (m, m 2H), 3.49 (s, 2H), 5.09 (s, 2H), 7.28 (m, 4H), 8.16 (m, 1H), 12.45 (br s, 2H).

후처리

  1. filtrationThe mixture was then filtered
  2. additionthe filtrate was added to an ice bath
  3. stirringThe resulting mixture was stirred at 0° C. for 30 min
  4. waitat rt for 2 hr
  5. customThe reaction was quenched by the addition of water (30 mL)
  6. concentrationthe resulting mixture was concentrated
  7. stirringThe residue was stirred with water (40 mL)
  8. filtrationthe resulting precipitate was collected through filtration
  9. customdried

출처 및 근거

ORD 기록
ord-017ba17c0fc54d9ab0d8a33f5cfce7fa
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09427475B2

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