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

HRID 1373110ノート

反応式

HRID 1373110 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b4a6e5d0fb2c47d2a8d0725a3b3effb1
出典データセット
uspto-grants-2007_01
特許番号
US07160905B2

反応ノート

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