Ammonium Chloride → (3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate

HRID 879232

반응식

HRID 879232 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:20]([O:24][C:25](=[O:37])[CH2:26][C@@H:27]([O:35][CH3:36])[C@@H:28]([NH:33][CH3:34])[C@@H:29]([CH3:32])[CH2:30][CH3:31])([CH3:23])([CH3:22])[CH3:21].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[C:20]([O:24][C:25](=[O:37])[CH2:26][C@@H:27]([O:35][CH3:36])[C@@H:28]([N:33]([C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:34])[C@@H:29]([CH3:32])[CH2:30][CH3:31])([CH3:22])([CH3:21])[CH3:23]

참가 물질

9

반응물 6

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 726987N-Carbobenzoxy-L-valine2회HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2회HCID 27960291-Hydroxybenzotriazole hydrate2회HCID 14730240(3r,4s,5s)-Tert-butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride2회

생성물 1

HCID 10529182(3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

425 mg (1.7 mmol) N-[(benzyloxy)carbonyl]-L-valine were dissolved in 50 ml of DMF and mixed successively with 500 mg (1.7 mmol) of tert.-butyl-(3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)-heptanoate hydrochloride (starting compound 2), 356 mg (1.9 mmol) 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride, 285 mg (1.9 mmol) 1-hydroxy-1H-benzotriazol hydrate and 655 mg (5.1 mmol) of N,N-iiisopropylethylamine. The mixture was stirred for 20 h at RT. Another 142 mg (0.5 mmol) of N-[(benzyloxy)carbonyl]-L-valine, 119 mg (0.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 95 mg (0.6 mmol) of 1-hydroxy-1H-benzotriazol hydrate and 218 mg (1.7 mmol) N,N-diisopropylethylamine were added and the mixture was treated with ultrasound for 90 min. The mixture was then poured into a solution of semi-saturated aqueous ammonium chloride and ethyl acetate. The organic phase was separated off, washed successively with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution, then dried over magnesium sulphate, filtered and evaporated. The remainder was purified using preparative HPLC. 329 mg (40% o. th.) of the title compound were obtained as a colorless oil.

후처리

  1. additionthe mixture was treated with ultrasound for 90 min
  2. customThe organic phase was separated off
  3. washwashed successively with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe remainder was purified

출처 및 근거

ORD 기록
ord-7aa6229f673f4f46bad25b640104f9e8
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987209B2

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