Water → HCID 71060529、化合物

HRID 1036738

反応式

HRID 1036738 の反応式
O=C1CCC(=O)N1[C:8](=[O:20])[C:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])[CH3:10].[NH2:21][C@H:22]([C@@H:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:27])[C:23]([OH:25])=[O:24].O>C1COCC1>[CH2:29]([O:28][C@@H:26]([CH3:27])[C@@H:22]([NH:21][C:8](=[O:20])[C:9]([NH:12][C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19])([CH3:11])[CH3:10])[C:23]([OH:25])=[O:24])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

5

反応物 3

HCID 962WaterHCID 22869571O-Benzyl-D-threonineHCID 71060486HCID 71060486、化合物

生成物 1

HCID 71060529HCID 71060529、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A mixture comprising of tert-butyl 1-(2,5-dioxopyrrolidin-1-yl)-2-methyl-1-oxopropan-2-ylcarbamate (1 g, 3.33 mmol) (prepared according to the procedure described in EP1486498A1 page 20) and (2R,3S)-2-amino-3-(benzyloxy)butanoic acid (0.697 g, 3.33 mmol) in THF (40 ml)/water (10 ml) was treated with TEA (1.392 ml, 9.99 mmol) and stirred at 50° C. for 4 hours. The resulting mixture was concentrated in vacuo and EtOAc (20 ml) was added. The pH was adjusted to pH2 with 1M HCl. The organic portion was separated and the aqueous phase was back extracted with EtOAc (30 ml). The combined organic portions were washed with a saturated solution of brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in DCM and concentrated in vacuo to afford the title compound.

後処理

  1. concentrationThe resulting mixture was concentrated in vacuo and EtOAc (20 ml)
  2. additionwas added
  3. customThe organic portion was separated
  4. extractionthe aqueous phase was back extracted with EtOAc (30 ml)
  5. washThe combined organic portions were washed with a saturated solution of brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in DCM
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e4bac0c5cb0548f7a485dab0aeaa5f6d
出典データセット
uspto-grants-2013_10
特許番号
US08546416B2

関連ノート

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