Trifluoroacetic anhydride → HCID 68311038, 화합물

HRID 529588노트

반응식

HRID 529588 반응식
C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.[NH2:14][C:15](=O)[CH2:16][C@H:17]([C:47](=[O:65])[NH:48][C@H:49]1[CH2:55][CH2:54][S:53][C@H:52]2[CH2:56][CH2:57][CH2:58][C@@H:59]([C:60]([O:62][CH3:63])=[O:61])[N:51]2[C:50]1=[O:64])[CH2:18][CH2:19][C@H:20]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:21]([NH:23][C@H:24]1[CH2:30][CH2:29][S:28][C@H:27]2[CH2:31][CH2:32][CH2:33][C@@H:34]([C:35]([O:37][CH3:38])=[O:36])[N:26]2[C:25]1=[O:39])=[O:22]>C(Cl)Cl>[CH2:40]([C@@H:20]([CH2:19][CH2:18][C@H:17]([CH2:16][C:15]#[N:14])[C:47]([NH:48][C@H:49]1[CH2:55][CH2:54][S:53][C@H:52]2[CH2:56][CH2:57][CH2:58][C@@H:59]([C:60]([O:62][CH3:63])=[O:61])[N:51]2[C:50]1=[O:64])=[O:65])[C:21]([NH:23][C@H:24]1[CH2:30][CH2:29][S:28][C@H:27]2[CH2:31][CH2:32][CH2:33][C@@H:34]([C:35]([O:37][CH3:38])=[O:36])[N:26]2[C:25]1=[O:39])=[O:22])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

참가 물질

4

반응물 2

HCID 9845Trifluoroacetic anhydrideHCID 68311207HCID 68311207, 화합물

생성물 1

HCID 68311038HCID 68311038, 화합물수율 52.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFAA (15 mg, 0.069 mmol) was slowly added to a 0° C. solution of Example 29 (27 mg, 0.034 mmol) and TEA (12.2 mg, 0.121 mmol) in DCM (0.25 mL). The reaction mixture was then stirred at rt for 1.5 hr. The reaction mixture was concentrated and the residue was partitioned between EtOAc and 10% aqueous Na2CO3. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The crude product was purified by RP prep-HPLC (Method A) to give dimethyl (4S,7S,10aS,4′S,7′S,10a′S)-4,4′-(((2R,5R)-2-benzyl-5-(cyanomethyl)-1,6-dioxo-1,6-hexanediyl)diimino)bis(5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate) (13 mg, 0.018 mmol, 51% yield). Anal. Calcd. for C37H49N5O8S2 m/z 755.7. found: 756.2 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.74 (1H, d, J=6.6 Hz), 7.30-7.21 (3H, m), 7.20-7.11 (3H, m), 5.44-5.35 (2H, m), 5.18-5.00 (4H, m), 3.72 (3H, s), 3.69 (3H, s), 3.20 (1H, ddd, J=14.0, 10.7, 2.7 Hz), 3.15-3.01 (3H, m), 2.96 (1H, ddd, J=14.4, 7.0, 2.7 Hz), 2.91-2.82 (2H, m), 2.71 (1H, dd, J=13.2, 6.6 Hz), 2.65-2.55 (2H, m), 2.53-2.35 (4H, m), 2.25 (1H, ddd, J=10.7, 6.9, 3.3 Hz), 2.09-1.96 (4H, m), 1.82 (1H, td, J=7.1, 3.8 Hz), 1.78-1.51 (10H, m).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc and 10% aqueous Na2CO3
  3. customThe organic phase was isolated
  4. washwashed with saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by RP prep-HPLC (Method A)

출처 및 근거

ORD 기록
ord-c8f6821f17de443b85eafd6915127415
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346852B2

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