Triethylamine → (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

HRID 1180446ノート

反応式

HRID 1180446 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:13])=O)=[CH:4][CH:3]=1.CN(C(O[N:32]1N=[N:39][C:34]2C=CC=N[C:33]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.Cl.NCC#N.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:11]([NH:39][CH2:34][C:33]#[N:32])=[O:13])=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11491918Aminoacetonitrile hydrochlorideHCID 69470808(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid

生成物 1

HCID 10319660(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid from Step 2, Example 1, (46.5 g, 123 mmol) was dissolved in DMF (200 mL). To this mixture was added HATU (56.7 g, 149 mmol, 1.2 eg), Et3N (57.7 g, 570 mmol, 4.6 eg), then added at 0° C. aminoacetonitrile hydrochloride (13.5 g, 146 mmol, 1.19 eg). The resulting reaction mixture was stirred at room temperature for 3 hours; then poured into 1 L of half saturated sodium bicarbonate. The aqueous phase was extracted with EtOAc (2×500 mL). Organic fraction was washed with brine (200 mL), INHCl (200 mL), brine (200 mL), 0.5 N NaOH (300 mL), brine (200 mL). Solvent was evaporated under reduced pressure and the resulting dark red oil which was chromatographed with 20% EA/hexane to give the title compound.

後処理

  1. customThe resulting reaction mixture
  2. extractionThe aqueous phase was extracted with EtOAc (2×500 mL)
  3. washOrganic fraction was washed with brine (200 mL), INHCl (200 mL), brine (200 mL), 0.5 N NaOH (300 mL), brine (200 mL)
  4. customSolvent was evaporated under reduced pressure
  5. customthe resulting dark red oil which was chromatographed with 20% EA/hexane

出典と根拠

ORDレコード
ord-8319d1725fe347bb97db850a17cbac37
出典データセット
uspto-grants-2007_10
特許番号
US07279478B2

反応ノート

読み込み中…