Diisopropylethylamine → Methyl (S)-2-[(6-azaspiro[2.5]octane-6-carbonyl)amino]-4,4-difluoropentanoate

HRID 1664728

反応式

HRID 1664728 の反応式
FC(F)(F)C(O)=O.[CH2:8]1[C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:9]1.CCN(C(C)C)C(C)C.[F:25][C:26]([F:37])([CH3:36])[CH2:27][C@H:28]([N:33]=[C:34]=[O:35])[C:29]([O:31][CH3:32])=[O:30]>ClC(Cl)C.ClCCl>[CH2:9]1[C:10]2([CH2:15][CH2:14][N:13]([C:34]([NH:33][C@@H:28]([CH2:27][C:26]([F:25])([F:37])[CH3:36])[C:29]([O:31][CH3:32])=[O:30])=[O:35])[CH2:12][CH2:11]2)[CH2:8]1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 57946243Methyl (S)-4,4-difluoro-2-isocyanatopentanoateHCID 666613976-Azaspiro[2.5]octane trifluoroacetate

生成物 1

HCID 57946179Methyl (S)-2-[(6-azaspiro[2.5]octane-6-carbonyl)amino]-4,4-difluoropentanoate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 63651,1-Dichloroethane溶媒2 回

実験手順

A solution of 0.75 g of 6-azaspiro[2.5]octane trifluoroacetate (3.30 mmol, 1 eq.) and 0.75 ml of DIPEA (1.3 eq.) in 6 ml of dichloroethane was added under argon to a solution of 0.65 g of methyl (S)-4,4-difluoro-2-isocyanatopentanoate (3.36 mmol) in 4 ml of dichloroethane. The reaction mixture was stirred at RT overnight. The mixture was diluted with 10 ml of dichloromethane and washed with saturated NaHCO3 solution. The organic phase was dried over MgSO4 and then concentrated under reduced pressure. The residue thus obtained was purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA. The product-containing fractions were combined and freeze-dried.

後処理

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by preparative HPLC (gradient
  6. additionacetonitrile/water and addition of 0.05% TFA
  7. customfreeze-dried

出典と根拠

ORDレコード
ord-060e81a68b014fbd9eeb2227556ecdf1
出典データセット
uspto-grants-2011_10
特許番号
US08039480B2

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