Sodium Carbonate → (+/-)-1,1-Dimethylethyl(3r,4s)-3-fluoro-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate

HRID 639096ノート

反応式

HRID 639096 の反応式
O[C@H:2]1[C@@H:6]([CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3]1.CCN(S(F)(F)[F:32])CC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[F:32][C@@H:2]1[C@@H:6]([CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 59254350rac-tert-butyl (3R,4R)-3-({[(benzyloxy)carbonyl]amino}methyl)-4-hydroxypyrrolidine-1-carboxylate

生成物 1

HCID 59026199(+/-)-1,1-Dimethylethyl(3r,4s)-3-fluoro-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of (±)-1,1-dimethylethyl cis-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (0.8 g, 2.29 mmole), in DCM (50 mL) at −78° C. was added DAST dropwise (0.59 mL, 4.80 mmole). After 2 h, Aqueous Na2CO3 was added to the reaction solution and the layers separated. The organic layer was dried over Na2SO4 and concentrated under vacuum. Purification on silica (hexanes/EtOAc, 1:1) provided the title compound (0.68 g, 85%) as a colorless oil: LC-MS (ES) m/e 353 (M+H)+.

後処理

  1. customthe layers separated
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customPurification on silica (hexanes/EtOAc, 1:1)

出典と根拠

ORDレコード
ord-65459450e185423d98e2794e1fc0fd20
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

反応ノート

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