Hydrochloric Acid → (2S)-1-(1,2-Dioxo-3,3-dimethylpentyl)azetidine-2-carboxylic acid

HRID 1264470ノート

反応式

HRID 1264470 の反応式
C[O:2][C:3]([C@@H:5]1[CH2:8][CH2:7][N:6]1[C:9](=[O:17])[C:10](=[O:16])[C:11]([CH3:15])([CH3:14])[CH2:12][CH3:13])=[O:4].CCOCC.[Li+].[OH-].Cl>O.CO>[O:17]=[C:9]([N:6]1[CH2:7][CH2:8][C@H:5]1[C:3]([OH:4])=[O:2])[C:10](=[O:16])[C:11]([CH3:14])([CH3:15])[CH2:12][CH3:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 59049321(2S)-Methyl-1-(1,2-dioxo-3,3-dimethylpentyl)-azetidine-2-carboxylate

生成物 1

HCID 59049304(2S)-1-(1,2-Dioxo-3,3-dimethylpentyl)azetidine-2-carboxylic acid収率 67%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of (2S)-Methyl-1-(1,2-dioxo-3,3-dimethylpentyl)-azetidine-2-carboxylate from Reference Example 3 (0.64 g, 2.65 mmol) in a 1:1 mixture of ether:methanol (20.0 mL) was added LiOH in water (4.9 mL, 1N solution) at about 0° C. The mixture was stirred at about 0° C. for about 30 minutes and then at about room temperature overnight. The pH was adjusted to about pH 1 by adding 1N HCl, then the mixture was diluted with water and extracted with dichloromethane. The organic layers were washed with brine and dried over sodium sulfate and then concentrated to give 0.40 g (67% yield) of the product as a yellow semisolid. 1H NMR (DMSO) δ 0.77-0.83 (m, 3H); 1.20-1.29 (series of s, 6H); 1.49-2.84 (series of m, 4H); 4.02-4.43 (series of m, 2H); 5.01-5.31 (series of dd, 1H); 6.10-6.80 (br, 1H).

後処理

  1. customat about room temperature
  2. customovernight
  3. extractionextracted with dichloromethane
  4. washThe organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-72421745bf2e45eb972db3ffbc71cdf1
出典データセット
uspto-grants-2003_04
特許番号
US06544976B1

反応ノート

読み込み中…