2-Amino-2-phenylethan-1-ol → (S)-(+)-3,4-dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone

HRID 1385025노트

반응식

HRID 1385025 반응식
[C:1]1([C:16]2[CH:21]=[CH:20]C=CC=2)[CH:6]=[CH:5][C:4]([C@@:7]2([CH3:15])[O:11][C:10](=[O:12])[C:9]([OH:13])=[C:8]2[OH:14])=[CH:3][CH:2]=1.[CH2:22](C1C=CC(C(C(OCC)=O)=O)=CC=1)C(C)C.C1C=CC([C@H](N)CO)=CC=1.C(C1C=CC([C@H](C)C(OC)=O)=CC=1)C(C)C>>[OH:13][C:9]1[C:10](=[O:12])[O:11][C@@:7]([CH3:15])([C:4]2[CH:3]=[CH:2][C:1]([CH2:16][CH:21]([CH3:20])[CH3:22])=[CH:6][CH:5]=2)[C:8]=1[OH:14]

참가 물질

5

반응물 4

HCID 1347972-Amino-2-phenylethan-1-olHCID 6933487Methyl (alphaS)-alpha-methyl-4-(2-methylpropyl)benzeneacetateHCID 12585534Ethyl 4-iso-butylbenzoylformateHCID 70247173(R)-(-)-5-[(1,1'-Biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone

생성물 1

HCID 70247960(S)-(+)-3,4-dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone수율 19%

실험 절차

(S)-(+)-3,4-Dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone was synthesized in an analogous manner used for the production of (R)-(−)-5-[(1,1′-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone starting with ethyl 4-isobutylbenzoylformate. (S)-(+)-Phenylglycinol was used to resolve the methyl (S)-(+)-2-(4-isobutylphenyl)propionate enantiomer, of which 1.2 g (5 mmol) was converted into 250 mg (19% yield) of (S)-(+)-3,4-dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone as a white crystalline material: mp 175-177° C. dec. (CHCl3/hexanes); [α]25D+132° (c=1.55; MeOH) 1H NMR (acetone-d6) δ 7.44-7.14 (m, 4H), 2.48 (d. 2H, J=7.1 Hz), 1.87-1.82 (m, 1H), 1.83 (s, 3H), 0.88 (d, 6H, J=6.5 Hz). Anal Calcd for C15H18O4: C, 68.68; H, 6.92. Found: C, 68.08; H, 6.90.

후처리

  1. custom(S)-(+)-3,4-Dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone was synthesized in an analogous manner

출처 및 근거

ORD 기록
ord-60f0304b37e94492ad3750fc635a3165
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262073B1

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