Triethylamine → [1-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl]-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester

HRID 1716873ノート

反応式

HRID 1716873 の反応式
[Cl-].[CH2:2]([CH:9]([NH3+:28])[CH:10]([OH:27])[CH2:11][N:12]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[O:36]1[CH:40]2[O:41][CH2:42][CH2:43][CH:39]2[CH:38]([O:44][C:45](=O)[O:46]N2C(=O)CCC2=O)[CH2:37]1>>[O:36]1[CH:40]2[O:41][CH2:42][CH2:43][CH:39]2[CH:38]([O:44][C:45](=[O:46])[NH:28][CH:9]([CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:10]([OH:27])[CH2:11][N:12]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:37]1

参加物

4

反応物 3

HCID 8471TriethylamineHCID 17981482Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl esterHCID 685086951-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride

生成物 1

HCID 66769651[1-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl]-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester

実験手順

A solution of 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride (4) (29.70 g, 72.90 mmol, 1 equiv), triethylamine (22.00 g, 220 mmol, 3 equiv) and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo-[2,3b]furan-3-yl ester (19.80 g, 73.00 mmol, 1 equiv) in 120 mL of dichlomethane were stirred at ambient temperature. Due to the incompleteness of the reaction, carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (5.00 g, 18.43 mmol) was added to the solution. The solution was stirred at room temperature for 24 h. The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution. The organic layer was dried on MgSO4, filtered, and evaporated to dryness to obtain the desired product as a white solid. (37.04 g, 70.34 mmol, 96.4%). LRMS (ES+): m/z 527 [M+H]+.

後処理

  1. additionwas added to the solution
  2. washThe solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution
  3. customThe organic layer was dried on MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-28f8573f0dcb44be88582a3079a14c44
出典データセット
uspto-grants-2010_09
特許番号
US07803836B2

反応ノート

読み込み中…