Hydrochloric Acid → 1-[(Tert-butoxy)carbonyl]-3-(ethoxycarbonyl)azetidine-3-carboxylic acid

HRID 1175125노트

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HRID 1175125 반응식
[CH2:1]([O:3][C:4]([C:6]1([C:17]([O:19]CC)=[O:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5])[CH3:2].[OH-].[Na+].Cl>CCO.O>[CH2:1]([O:3][C:4]([C:6]1([C:17]([OH:19])=[O:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:7]1)=[O:5])[CH3:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 574158971-tert-Butyl 3,3-diethyl azetidine-1,3,3-tricarboxylate

생성물 1

HCID 574158841-[(Tert-butoxy)carbonyl]-3-(ethoxycarbonyl)azetidine-3-carboxylic acid

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

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온도
50 °C

실험 절차

Azetidine-1,3,3-tricarboxylic acid 1-tert-butyl ester 3,3-diethyl ester (1.2 g; 0.4 mmol) in EtOH (12 ml) is cooled to 5° C. under stirring and combined with NaOH (60 mg; 0.04 mmol) in water (4 ml). The reaction mixture is left at room temperature for 1 hour, heated to 50° C. for 5 minutes, poured on brine, acidified with 2N HCl and extracted with TBME three times. The reaction mixture is extracted with TBME three times, the organic phases are combined, dried over Na2SO4 and evaporated to dryness, yielding the desired product as colorless crystals. 1H-NMR (400 MHz; DMSO-d6: 13.58 (bs, 1H); 4.20 (q, 2H); 4.12 (bs, 4H); 1.39 (s, 9H); 1.21 (t, 3H). MS (m/z) ES+: 274 (30; MH+); 174 (100).

후처리

  1. additionpoured on brine
  2. extractionextracted with TBME three times
  3. extractionThe reaction mixture is extracted with TBME three times
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-7b7fe557d6e54555857fb8942a1cfaf3
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838674B2

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