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

HRID 1175125ノート

反応式

HRID 1175125 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7b7fe557d6e54555857fb8942a1cfaf3
出典データセット
uspto-grants-2010_11
特許番号
US07838674B2

反応ノート

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