Boric Acid → Methyl 7-(4'-fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl)-3-hydroxy-5-oxoheptanoate

HRID 344827노트

반응식

HRID 344827 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2[CH2:16][CH2:17][C:18]2[CH2:22][CH:21]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[O:20]N=2)=[CH:4][C:3]=1[CH3:28].B(O)(O)[OH:30]>[Pd].CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2[CH2:16][CH2:17][C:18](=[O:30])[CH2:22][CH:21]([OH:20])[CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:4][C:3]=1[CH3:28]

참가 물질

6

반응물 2

HCID 7628Boric AcidHCID 54381644Methyl 3-[2-(4'-fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-yl)ethyl]-4,5-dihydro-5-isoxazoleacetate

생성물 1

HCID 67947384Methyl 7-(4'-fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl)-3-hydroxy-5-oxoheptanoate

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 962Water용매

실험 절차

A mixture of 0.1 g (0.26 mmol) of the isoxazoline from Step E, 50 mg of 10% palladium on carbon catalyst and 48 mg (0.78 mmol) of boric acid in 3 ml of methanol and 0.3 ml of water was stirred under hydrogen (1 atmosphere) at room temperature for 2.5 hours. The mixture was filtered and the filtrate was poured into brine and extracted with ether. The ethereal extract was washed with 5% (w/v) aqueous sodium bicarbonate solution, dried (MgS04), filtered and evaporated to dryness to give 92 mg (0.23 mmol, 89%) as a pale yellow oil. nmr (CDCl3) δ: 2.30 (6H, a methyl singlet and a methyl doublet), 2.33 (3H, s), 2.35-2.5 (6H, m), 2.75-2.85 (2H, m), 3.30 (H, d), 3.70 (3H, s), 4.37 (H, m), 6.83 (H, bs), 6.95-7.1 (4H, m). IR (neat) 3450, 1710 cm-1.

후처리

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was poured into brine
  3. extractionextracted with ether
  4. extractionThe ethereal extract
  5. washwas washed with 5% (w/v) aqueous sodium bicarbonate solution
  6. customdried (MgS04)
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customto give 92 mg (0.23 mmol, 89%) as a pale yellow oil

출처 및 근거

ORD 기록
ord-dc95b1de18ec42a1bc62220a212b868c
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05053525

반응 노트

불러오는 중…