Dicyclohexylcarbodiimide → HCID 54365840、化合物

HRID 482774ノート

反応式

HRID 482774 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH:14](O)[CH:13]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:12]2[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][CH:13]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:12]2[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 2

HCID 10868Dicyclohexylcarbodiimide2 回HCID 54529640HCID 54529640、化合物

生成物 1

HCID 54365840HCID 54365840、化合物

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-5-hydroxy-2,3,4,5,5a,6,7,8,9,9a-decahydro-1H-[1]benzazepin-2-one (2.1 g), dicyclohexylcarbodiimide (1.8 g) and cuprous chloride (0.2 g) is heated at 80° under nitrogen for 32 hours. The reaction mixture is cooled to room temperature, the residue is dissolved in methylene chloride (200 ml), washed with dilute ammonium hydroxide (2×50 ml) and water (50 ml). The organic phase is dried over sodium sulfate and evaporated to give a mixture of the desired adduct and excess dicyclohexylcarbodiimide. This mixture is dissolved in ethyl acetate (100 ml) and placed in a pressure bottle. 10% Pd/C (0.4 g) is added and the mixture hydrogenated at 3 atmospheres pressure and 40° for 16 hours. The catalyst is filtered off and the filtrate is evaporated to give 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-2,3,4,5,5a,6,7,8,9,9a-decahydro-1H-[1]benzazepin-2-one, used without further purification for the next synthetic step.

後処理

  1. temperatureis heated at 80° under nitrogen for 32 hours
  2. washwashed with dilute ammonium hydroxide (2×50 ml) and water (50 ml)
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customto give
  6. filtrationThe catalyst is filtered off
  7. customthe filtrate is evaporated

出典と根拠

ORDレコード
ord-6026b9fc2d7949f8975cfd5ab2664d78
出典データセット
uspto-grants-1986_03
特許番号
US04575503

反応ノート

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