Ammonia → Benzyl 3-({[(tert-butoxy)carbonyl]amino}methyl)-3-hydroxyazetidine-1-carboxylate

HRID 1808966노트

반응식

HRID 1808966 반응식
[O:1]1[C:3]2([CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[CH2:4]2)[CH2:2]1.[NH3:17].[C:18]([O:22][C:23]([O:25]C(OC(C)(C)C)=O)=O)([CH3:21])([CH3:20])[CH3:19]>C1COCC1>[CH3:19][C:18]([O:22][C:23]([NH:17][CH2:2][C:3]1([OH:1])[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:4]1)=[O:25])([CH3:21])[CH3:20]

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 90495Di-tert-butyl dicarbonateHCID 594692221-Oxa-5-azaspiro[2.3]hexane-5-carboxylic acid phenylmethyl ester

생성물 1

HCID 67051555Benzyl 3-({[(tert-butoxy)carbonyl]amino}methyl)-3-hydroxyazetidine-1-carboxylate수율 7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Phenylmethyl 1-oxa-5-azaspiro[2.3]hexane-5-carboxylate (165 mg, 0.75 mmol), prepared using procedures similar to those described in Reference 3, in THF (1 mL) was added to anhydrous ammonia saturated in THF (10 mL) and the mixture was allowed to stir in a sealed vessel at room temperature over 24 hours. The solution was then concentrated and taken back into THF (1 mL) followed by addition of di-tert-butyldicarbonate (164 mg, 0.75 mmol) and stirred for one hour at room temperature. The mixture was then concentrated and the residue purified by silica gel flash chromatography using hexanes:ethyl acetate (1:1) as eluent to give phenylmethyl 3-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-3-hydroxyazetidine-1-carboxylate (16.5 mg, 7% yield) and unreacted epoxide (120 mg, 73% recovery). 1H-NMR (400 MHz, CDCl3): 7.34 (m, 5H), 5.10 (br, 1H), 5.09 (s, 2H), 4.68 (s, 1H), 3.90 (dd AB, 4H), 3.41 (d, 2H), 1.44 (s, 9H).

후처리

  1. concentrationThe solution was then concentrated
  2. stirringstirred for one hour at room temperature
  3. concentrationThe mixture was then concentrated
  4. customthe residue purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-7d92f0c3bfdb4292b9e72ab1174dd24b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362002B2

반응 노트

불러오는 중…