Dicyclohexylcarbodiimide → HCID 54365840, 화합물

HRID 482774노트

반응식

HRID 482774 반응식
[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]

참가 물질

6

반응물 2

HCID 10868Dicyclohexylcarbodiimide2회HCID 54529640HCID 54529640, 화합물

생성물 1

HCID 54365840HCID 54365840, 화합물

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6026b9fc2d7949f8975cfd5ab2664d78
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04575503

반응 노트

불러오는 중…