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

HRID 1180446노트

반응식

HRID 1180446 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-8319d1725fe347bb97db850a17cbac37
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279478B2

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