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

HRID 879232

反応式

HRID 879232 の反応式
[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]

参加物

9

反応物 6

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 726987N-Carbobenzoxy-L-valine2 回HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2 回HCID 27960291-Hydroxybenzotriazole hydrate2 回HCID 14730240(3r,4s,5s)-Tert-butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7aa6229f673f4f46bad25b640104f9e8
出典データセット
uspto-grants-2015_03
特許番号
US08987209B2

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