1,2-Dichloroethane → tert-Butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-yl]carbamate

HRID 133129

반응식

HRID 133129 반응식
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C@@H:9]([C:23]([OH:25])=O)[CH2:10][CH2:11][C@@H:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[F:22])[CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:22][C:16]1[C:17]([F:21])=[CH:18][CH:19]=[CH:20][C:15]=1[C@H:12]1[CH2:13][NH:14][C:23](=[O:25])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][CH2:11]1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 67526479(5S)-N2,N2-Bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-D-lysine

생성물 1

HCID 23657400tert-Butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-yl]carbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution (5S)—N2,N2-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-D-lysine from Step D (22.0 g, 48.0 mmol) in CH2Cl2 (700 mL) were added EDC (11.0 g, 57.6 mmol) and HOAT (3.27 g, 24.0 mmol) followed by triethylamine (10.0 mL, 72.0 mmol). After 1 h, aqueous NaHCO3 was added, the layers were separated, and the aqueous phase was extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with CH2Cl2:MeOH—90:10, to give the title compound. MS: m/z=341 (M+1).

후처리

  1. customthe layers were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with CH2Cl2

출처 및 근거

ORD 기록
ord-558f8849205643dfa6130d05bee5202e
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390798B2

연결된 노트

불러오는 중…