HCID 67640328, 화합물 → HCID 67640683, 화합물

HRID 399516노트

반응식

HRID 399516 반응식
[C:1]([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][C@H:10]([C:12]#[N:13])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][C@@H:10]([CH2:12][NH2:13])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH3:3])([CH3:4])[CH3:2]

참가 물질

4

반응물 1

HCID 67640328HCID 67640328, 화합물

생성물 1

HCID 67640683HCID 67640683, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution (4S)-1-(tert-butyloxycarbonyl)-4-cyano-L-proline tert-butyl ester (470 mg, 1.59 mmol) in 90% ethanol (22 mL) was hydrogenated in the presence of 10% palladium-on-charcoal (225 mg) at 450 psi for 24 hours. The catalyst was removed by filtration through Celite, the filter washed with ethanol, and the combined filtrate and washings evaporated. Purification was achieved by flash silica gel chromatography eluting with 95:5:0.5 chloroform-methanol-ammonia; yield 284 mg (60%). 400 MHz 1H NMR (CD3OD): δ1.41-1.48 (3s, 18H); 1.58 (m, 1H); 2.28 (m, 1H); 2.48 (m, 1H); 2.66 (m, 2H); 3.05 (dd, 1H); 3.71 (dd, 1H); 4.12 (m, 1H).

후처리

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter washed with ethanol
  3. customthe combined filtrate and washings evaporated
  4. customPurification
  5. washeluting with 95:5:0.5 chloroform-methanol-ammonia

출처 및 근거

ORD 기록
ord-aeb7fd57321348fdb99c27347f87fcdb
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05821261

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