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

HRID 1488254

反応式

HRID 1488254 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-017ba17c0fc54d9ab0d8a33f5cfce7fa
出典データセット
uspto-grants-2016_08
特許番号
US09427475B2

関連ノート

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