Benzyl succinimido carbonate → Benzyl (2r)-3-(4-cyanophenoxy)-2-hydroxypropylcarbamate

HRID 411541ノート

反応式

HRID 411541 の反応式
[NH2:1][CH2:2][C@@H:3]([OH:14])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[CH2:15]([O:22][C:23](ON1C(=O)CCC1=O)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)(Cl)Cl.C(Cl)Cl>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][C@H:3]([OH:14])[CH2:2][NH:1][C:23](=[O:24])[O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:8]=1)#[N:11]

参加物

5

反応物 2

HCID 83172Benzyl succinimido carbonateHCID 300720964-{[(2R)-3-Amino-2-hydroxypropyl]oxy}benzonitrile

生成物 1

HCID 91135093Benzyl (2r)-3-(4-cyanophenoxy)-2-hydroxypropylcarbamate収率 100%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4{[(2R)-3-amino-2-hydroxypropyl]oxy}benzonitrile (see step (ii) above; 3.4 g, 17.7 mmol), TEA (2.69 g, 26.6 mmol) and CHCl3 (20 mL) was cooled to 0° C. before N-(benzyloxycarbonyloxy)succinimide (4.86 g, 19.5 mol) in CHCl3 (15 mL) was added slowly. The mixture was allowed to reach rt, and was stirred at that temperature overnight. The solvent was evaporated to give a residue that was dissolved in DCM. This solution was washed with water and brine and then dried (Na2SO4). Evaporation of the solvent gave 5.79 g (100%) of the sub-title compound.

後処理

  1. additionwas added slowly
  2. customto reach rt
  3. customThe solvent was evaporated
  4. customto give a residue that
  5. washThis solution was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-9df57f2bfb3e467fbbe6b80865b95060
出典データセット
uspto-grants-2003_05
特許番号
US06559162B2

反応ノート

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