Hydrochloric Acid → 1,1-Dimethylethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(hydroxymethyl)-1-azetidinecarboxylate

HRID 1175127ノート

反応式

HRID 1175127 の反応式
C([O:3][C:4]([C:6]1([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=O)C.[Li+].[BH4-].Cl>C1COCC1.O>[C:13]([O:12][C:10]([N:8]1[CH2:9][C:6]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH2:4][OH:3])[CH2:7]1)=[O:11])([CH3:15])([CH3:16])[CH3:14]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 57654649HCID 57654649、化合物

生成物 1

HCID 576546571,1-Dimethylethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(hydroxymethyl)-1-azetidinecarboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

3-tert-Butoxycarbonylamino-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (520 mg; 1.5 mmol) in THF (15 ml) is refluxed with LiBH4 (67 mg; 3 mmol) for 20 minutes. The reaction mixture is diluted with water, acidified with 2N HCl to destroy excess of LiBH4, neutralized again with 2N Na2CO3 and 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: 7.27 (bs, 1H); 5.07 (bt, 1H); 3.78 (bs, 4H); 3.46 (d, 2H); 1.40 (s, 9H); 1.38 (s, 9H). MS (m/z) ES+: 303 (MH+).

後処理

  1. customto destroy excess of LiBH4
  2. extractionextracted with TBME three times
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-631e08d2ce6143018552433957d395de
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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