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

HRID 1264470노트

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HRID 1264470 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-72421745bf2e45eb972db3ffbc71cdf1
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06544976B1

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