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Water → (R)-2-(2-(tert-Butoxycarbonylamino)-2-methylpropanamido)-4-phenylbutanoic acid

HRID 1036737
ノート
印刷プレビュー

反応式

HRID 1036737 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].[CH:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C@@H:29]([NH2:33])[C:30]([OH:32])=[O:31])=[CH:23][CH:22]=1.O.C(N(CC)CC)C>C1COCC1>[C:15]([O:14][C:13]([NH:12][C:9]([CH3:11])([CH3:10])[C:8]([NH:33][C@H:29]([CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][CH:21]=[CH:26][CH:25]=1)[C:30]([OH:32])=[O:31])=[O:20])=[O:19])([CH3:18])([CH3:17])[CH3:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 6950302D-HomophenylalanineHCID 71060486Tert-butyl 1-(2,5-dioxopyrrolidin-1-yl)-2-methyl-1-oxopropan-2-ylcarbamate

生成物 1

HCID 22862434(R)-2-(2-(tert-Butoxycarbonylamino)-2-methylpropanamido)-4-phenylbutanoic acid

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
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, 3.52 mmol) (prepared according to the procedure described in EP1486498A1 page 20) and H-D-Homophe-OH (0.630 g, 3.52 mmol) in THF (16 ml)/water (4 ml) was treated with triethylamine (1.471 ml, 10.55 mmol). The reaction mixture was stirred at 50° C. for 9 hours. THF was removed in vacuo. The aqueous solution was further diluted with water and the pH adjusted to pH 2-3 using 1M HCl. The resulting aqueous phase was extracted with EtOAc. The organic portion was dried (MgSO4) and concentrated in vacuo to afford the title compound.

後処理

  1. customTHF was removed in vacuo
  2. additionThe aqueous solution was further diluted with water
  3. extractionThe resulting aqueous phase was extracted with EtOAc
  4. dry with materialThe organic portion was dried (MgSO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-dc4a3cf71c9c482baed69d543722a3d6
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546416B2

反応ノート

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