Trifluoroacetic acid → (2S)-2-(3-benzyl-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoic acid

HRID 1174300ノート

反応式

HRID 1174300 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C@@H:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:14]([O:16]C(C)(C)C)=[O:15])[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C@@H:13]([C:21]([CH3:23])([CH3:22])[CH3:24])[C:14]([OH:16])=[O:15])[C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 67405684tert-butyl(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoate

生成物 1

HCID 42626247(2S)-2-(3-benzyl-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of the product of Example 111-5 in dichloromethane (1.5 L) was added triflouroacetic acid (810 mL). The mixture was stirred at room temperature for 3 hours and concentrated. The residue was chased with heptanes (4×500 mL). The product was partitioned between dichloromethane (1.5 L) and 5% KH2PO4 (1.1 L). The organic layer was washed with 5% KH2PO4 (900 mL) and brine (900 mL), and concentrated. A solution of the residue in dichloromethane (500 mL) was dried over MgSO4, filtered and concentrated. The residue was recrystallized twice from isopropyl alcohol/water to afford the title compound. 1H NMR (DMSO-d6): δ 7.2-7.4(m, 5H), 4.28(d, 2H), 4.21(s, 1H), 3.47-3.64(m, 2H), 3.08-3.2(m, 2H), 1.0(s, 9H).

後処理

  1. concentrationconcentrated
  2. customThe product was partitioned between dichloromethane (1.5 L) and 5% KH2PO4 (1.1 L)
  3. washThe organic layer was washed with 5% KH2PO4 (900 mL) and brine (900 mL)
  4. concentrationconcentrated
  5. dry with materialA solution of the residue in dichloromethane (500 mL) was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized twice from isopropyl alcohol/water

出典と根拠

ORDレコード
ord-0977f4b22d4244ef98751220588fc9e1
出典データセット
uspto-grants-2010_11
特許番号
US07834043B2

反応ノート

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