1,2-Dichloroethane → (S)-Methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

HRID 339232

반응식

HRID 339232 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C@H:17]1([NH:27][C:28]([C@@H:30]2[CH2:39][C:38]3[C:33](=[CH:34][C:35]([C:40]([O:42][CH3:43])=[O:41])=[CH:36][CH:37]=3)[CH2:32][NH:31]2)=[O:29])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([N:31]1[C@H:30]([C:28](=[O:29])[NH:27][C@H:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)[CH2:39][C:38]2[C:33](=[CH:34][C:35]([C:40]([O:42][CH3:43])=[O:41])=[CH:36][CH:37]=2)[CH2:32]1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acidHCID 86705866(S)-Methyl 3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

생성물 1

HCID 86705867(S)-Methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate수율 100.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 0° C. solution of (S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid (473 mg, 2.04 mmol) and (S)-methyl 3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate (745 mg, 2.04 mmol) in CH2Cl2 (12.4 mL) was added EDC (471 mg, 2.45 mmol), HOAt (334 mg, 2.45 mmol) and NMM (675 μL, 6.14 mmol). The resulting reaction mixture was allowed to warm to room temperature overnight and then quenched with EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (3×). The combined organic extracts were washed with 1N HCl (2×), sat. aq. NaCl solution (1×), dried over MgSO4, filtered and concentrated in vacuo to give the title compound (1.18 g, 2.045 mmol, 100%) as a light yellow foam, which was used without further purification. MS (ESI+) m/z 578.2 (M+H)+.

후처리

  1. customThe resulting reaction mixture
  2. customquenched with EtOAc and sat. NaHCO3
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washThe combined organic extracts were washed with 1N HCl (2×), sat. aq. NaCl solution (1×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ba98733d570d424eaf19d17e3eb317aa
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889712B2

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