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

HRID 1175127노트

반응식

HRID 1175127 반응식
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]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 57654649HCID 57654649, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-631e08d2ce6143018552433957d395de
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838674B2

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