1,1'-Carbonyldiimidazole → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-N-[(1S,2R)-3-chloro-1-benzyl-2-hydroxypropyl]carbamate

HRID 73815ノート

反応式

HRID 73815 の反応式
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[O:13]1[C@H:17]2[O:18][CH2:19][CH2:20][C@H:16]2[C@@H:15]([OH:21])[CH2:14]1.Cl.[NH2:23][C@@H:24]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@H:25]([OH:28])[CH2:26][Cl:27].N[C@@H](CC1C=CC=CC=1)[C@H](O)CCl>C1COCC1.C(OCC)(=O)C>[O:13]1[C@H:17]2[O:18][CH2:19][CH2:20][C@H:16]2[C@@H:15]([O:21][C:1](=[O:2])[NH:23][C@@H:24]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:25]([OH:28])[CH2:26][Cl:27])[CH2:14]1

参加物

7

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 9942150(3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-olHCID 11183945(2S,3S)-3-amino-1-chloro-2-hydroxy-4-phenylbutaneHCID 46703513(2S,3S)-3-Amino-1-chloro-4-phenylbutan-2-ol hydrochloride

生成物 1

HCID 86674032(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-N-[(1S,2R)-3-chloro-1-benzyl-2-hydroxypropyl]carbamate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

1,1′-carbonyldiimidazole (162.15 g, 1 mol) was added to THF (0.5 L), following by solution of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (135.2 g, 1.04 mol) in 0.3 L of THF and the mixture was stirred for a further hour. (2S,3S)-3-amino-1-chloro-2-hydroxy-4-phenylbutane hydrochloride (229 g, 0.97 mol) was added and the mixture heated at 55-60° C. approximately 5-6 hours under TLC control (for complete disappearance of (2S,3S)-3-amino-1-chloro-2-hydroxy-4-phenylbutane). After completion of reaction the solution was cooled and transformed to the next step. For the preparation of analytical sample, 10 ml of solution was diluted with 50 ml of ethyl acetate, washed with water (40 mL), diluted hydrochloric acid (40 ml), 5% aqueous sodium hydrogen carbonate (40 mL) and water (50 mL). The solution was dried over sodium sulfate and evaporated to dryness. MS: m/z 356 (MH+). NMR spectrum corresponded to the structure of the desired product.

後処理

  1. customAfter completion of reaction the solution
  2. temperaturewas cooled
  3. washwashed with water (40 mL), diluted hydrochloric acid (40 ml), 5% aqueous sodium hydrogen carbonate (40 mL) and water (50 mL)
  4. dry with materialThe solution was dried over sodium sulfate
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-c7dab20f920243519d7e00efb131103e
出典データセット
uspto-grants-2014_09
特許番号
US08829208B2

反応ノート

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