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

HRID 1808966ノート

反応式

HRID 1808966 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7d92f0c3bfdb4292b9e72ab1174dd24b
出典データセット
uspto-grants-2013_01
特許番号
US08362002B2

反応ノート

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