1-Hydroxybenzotriazole → N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-methanesulfonyl-benzamide

HRID 1373110노트

반응식

HRID 1373110 반응식
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)(=[O:4])=[O:3].ON1C2C=CC=CC=2N=N1.[CH3:24][C:25]([CH3:46])([CH3:45])[CH2:26][CH2:27][NH:28][C:29](=[O:44])[C@H:30]([CH3:43])[CH2:31][C@H:32]([OH:42])[C@@H:33]([NH2:41])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C=O)C>[CH2:34]([C@H:33]([NH:41][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=1)[C@@H:32]([OH:42])[CH2:31][C@H:30]([C:29](=[O:44])[NH:28][CH2:27][CH2:26][C:25]([CH3:24])([CH3:45])[CH3:46])[CH3:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 2203803-Methanesulfonylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68890142(2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)-amide

생성물 1

HCID 58780868N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-methanesulfonyl-benzamide수율 39.2%

시약·촉매·용매 1

HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

To a solution of 3-methanesulfonyl benzoic acid (77 mg, 0.39 mmol) and 1-hydroxybenzotriazole (52 mg, 0.39 mmol) in 2:1 dichloromethane/DMF (3.0 ml) was added (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)-amide (D2) (100 mg, 0.32 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (86 mg, 0.45 mmol). The resulting solution was stirred at room temperature overnight and then evaporated to dryness. The residue was partitioned between ethyl acetate and 1M hydrochloric acid. The organic phase was separated and washed with further 1M hydrochloric acid, dil. aq. NaHCO3 and brine. It was dried over MgSO4, filtered and evaporated to afford the crude product which was triturated with ether to afford the title compound (63 mg, 39%).

후처리

  1. customevaporated to dryness
  2. customThe residue was partitioned between ethyl acetate and 1M hydrochloric acid
  3. customThe organic phase was separated
  4. washwashed with further 1M hydrochloric acid, dil. aq. NaHCO3 and brine
  5. dry with materialIt was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product which
  9. customwas triturated with ether

출처 및 근거

ORD 기록
ord-b4a6e5d0fb2c47d2a8d0725a3b3effb1
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160905B2

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