Triethylamine → HCID 44576654、化合物

HRID 1095386ノート

反応式

HRID 1095386 の反応式
[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].C(N(CC)CC)C.Cl[C:24](OC1C=CC([N+]([O-])=O)=CC=1)=[O:25].[NH2:36][C@H:37]([C:42]([NH2:44])=[O:43])[C:38]([CH3:41])([CH3:40])[CH3:39]>ClCCl>[NH2:44][C:42]([C@@H:37]([NH:36][C:24]([N:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:5]([CH2:4][CH2:3][CH:2]([CH3:15])[CH3:1])[C:6]1=[O:14])=[O:25])[C:38]([CH3:41])([CH3:40])[CH3:39])=[O:43]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 7096671,3-Dihydro-1-(3-methylbutyl)-2H-benzimidazol-2-oneHCID 11297986(2S)-2-Amino-3,3-dimethylbutanamide

生成物 1

HCID 44576654HCID 44576654、化合物収率 96.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 1-(3-methylbutyl)1,2-dihydro-2H-benzimidazol-2-one (Step 1, 140 mg, 0.69 mmol) in dichloromethane (2.5 mL) were added triethylamine (0.32 mL, 2.3 mmol) and 4-nitrophenyl chloroformate (150 mg, 0.76 mmol) at 0° C. and the mixture was stirred for 4 h at rt. Then to this mixture was added a solution of L-tert-leucinamide (steps 1 and 2 in example 4, 99 mg, 0.76 mmol) in dichloromethane (2 mL) at 0° C. and stirred rt. After 22 h, the reaction was quenched by addition of water (20 mL) and extracted with ethyl acetate (30 mL×2). The combined organic layers were washed with water (20 mL×3), brine (20 mL) and dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3/1-1/1) to afford 240 mg (96%) of the titled compound. The obtained product was further purified by recrystallization from hexane/ethyl acetate to give 220 mg of the title compound.

後処理

  1. stirringstirred rt
  2. waitAfter 22 h
  3. customthe reaction was quenched by addition of water (20 mL)
  4. extractionextracted with ethyl acetate (30 mL×2)
  5. washThe combined organic layers were washed with water (20 mL×3), brine (20 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3/1-1/1)

出典と根拠

ORDレコード
ord-00253e36885a4e80a29ef2f6a0f2b23f
出典データセット
uspto-grants-2012_03
特許番号
US08138177B2

反応ノート

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