Water → HCID 58487946、化合物

HRID 1677786ノート

反応式

HRID 1677786 の反応式
[CH3:1][C:2]1([CH3:27])[O:6][C@@H:5]([C@H:7]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:8]([O:10]C2C(F)=C(F)C(F)=C(F)C=2F)=O)[C:4](=[O:26])[O:3]1.ONC(=O)[C@@H](O)[C@@H](C(N1CCN(C2C=CC=CN=2)CC1)=O)CC(C)C.ONC(=O)[C@@H](O)[C@@H](C([N:64]1[CH2:69][CH2:68][N:67]([C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][N:71]=2)[CH2:66][C@H:65]1[CH3:76])=O)CC(C)C.O>CN(C=O)C>[CH3:27][C:2]1([CH3:1])[O:3][C:4](=[O:26])[C@H:5]([C@@H:7]([C:8]([N:64]2[CH2:69][CH2:68][N:67]([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][N:71]=3)[CH2:66][C@@H:65]2[CH3:76])=[O:10])[CH2:22][CH:23]([CH3:24])[CH3:25])[O:6]1

参加物

6

反応物 4

HCID 962WaterHCID 11653205HCID 11653205、化合物2 回HCID 11660575HCID 11660575、化合物2 回HCID 86617975HCID 86617975、化合物

生成物 1

HCID 58487946HCID 58487946、化合物収率 22%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of a 55/45 diastereoisomeric mixture of pentafluorophenyl (2S)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate and pentafluorophenyl (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate (Intermediate 1, 198 mg; 0.50 mmol; 1.0 eq.) in DMF (4 mL) was added (3S)-3-methyl-1-pyridin-2-ylpiperazine (Intermediate 4, 88.6 mg; 0.50 mmol; 1.0 eq.) and the resulting reaction mixture was stirred 48 h at RT. Water was added and the mixture was extracted with Et2O. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated to give an oil. Purification by chromatography (SiO2, gradient from 10% EtOAc in c-hex up to 40% EtOAc in c-hex in 15 min) gave the title compound as a colorless oil (43 mg; 22%) (mixture of 2 diastereoisomers). M+(ESI): 390.3.

後処理

  1. customthe resulting reaction mixture
  2. extractionthe mixture was extracted with Et2O
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give an oil
  8. customPurification by chromatography (SiO2, gradient from 10% EtOAc in c-hex up to 40% EtOAc in c-hex in 15 min)

出典と根拠

ORDレコード
ord-65375841305b49c28bf4af21bd25b1da
出典データセット
uspto-grants-2011_08
特許番号
US08008302B2

反応ノート

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