Hydrochloric Acid → HCID 57594555、化合物

HRID 730336ノート

反応式

HRID 730336 の反応式
[OH:1][CH2:2][CH2:3][C@@H:4]([NH:24][C:25](=[O:31])OC(C)(C)C)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[C:19]([CH:20]([OH:22])[CH3:21])=[CH:18][CH:17]=[CH:16][N:15]3[CH:23]=2)=[CH:8][CH:7]=1.Cl.O1CCOCC1.C(N(CC)C(C)C)(C)C.[Cl:48][C:49]1[CH:50]=[C:51]([CH:66]=[CH:67][C:68]=1[O:69][CH:70]([CH3:72])[CH3:71])C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>O>[Cl:48][C:49]1[CH:50]=[C:51]([CH:66]=[CH:67][C:68]=1[O:69][CH:70]([CH3:72])[CH3:71])[C:25]([NH:24][C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[C:14]3[C:19]([CH:20]([OH:22])[CH3:21])=[CH:18][CH:17]=[CH:16][N:15]3[CH:23]=2)=[CH:10][CH:11]=1)[CH2:3][CH2:2][OH:1])=[O:31]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 57594128HCID 57594128、化合物HCID 57594302HCID 57594302、化合物

生成物 1

HCID 57594555HCID 57594555、化合物収率 53%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 1,1-dimethylethyl [(1S)-3-hydroxy-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)propyl]carbamate (1.08 g, 2.54 mmol) and 4M HCl in 1,4-dioxane (8.0 mL, 32 mmol) was stirred at room temperature for 30 minutes. The reaction was concentrated to dryness, redissolved in DMF (25 mL), and to this solution was added N,N-diisopropylethylamine (1.64 g, 12.7 mmol) and pentafluorophenyl 3-chloro-4 [(1-methylethyl)oxy]benzoate (0.963 g, 2.54 mmol). The mixture was stirred for 3.0 h at room temperature, diluted with water, and extracted into ethyl acetate. The extracts were washed with water and saturated sodium chloride, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (2% MeOH:EtOAc) to give the title compound (0.7 g, 53%) as a pale yellow powder. MS(ES+) m/e 522 [M+H]+.

後処理

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionredissolved in DMF (25 mL)
  3. stirringThe mixture was stirred for 3.0 h at room temperature
  4. extractionextracted into ethyl acetate
  5. washThe extracts were washed with water and saturated sodium chloride
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (2% MeOH:EtOAc)

出典と根拠

ORDレコード
ord-0d6823e7df924fc6804db671b3055a3e
出典データセット
uspto-grants-2009_09
特許番号
US07582668B2

反応ノート

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