2-Amino-2-phenylethan-1-ol → (R)-(-)-5-[(1,1'-Biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone

HRID 369159Notes

Reaction equation

HRID 369159 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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.C1(C2C=CC=CC=2)C=CC([C@](O)(C)C(O)=O)=CC=1.C1C=CC([C@H](N)CO)=CC=1>>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=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

Participants

4

Reactant 3

HCID 1347972-Amino-2-phenylethan-1-olHCID 53697009(R)-(-)-2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionic acidHCID 70246787(S)-(+)-5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone

Product 1

HCID 70247173(R)-(-)-5-[(1,1'-Biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone

Procedure

(R)-(-)-5-[(1,1'-Biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone was prepared in an analogous manner as described for (S)-(+)-5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone starting with 1.9 g (5.0 mmol) of the diastereomerically pure salt of (R)-(-)-2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionic acid and (S)-(+)-phenylglycinol to provide 280 mg (19% yield) of(R)-(-)-5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone as a white crystalline material: mp 197-199° C. dec. (CHCl3 /hexanes); [α]25D -182° (c=1.42; MeOH); 1H NMR (acetone-d6) δ 7.65-7.41 (m, 9H), 1.89 (s, 3H). Anal Calcd for C17H14O4 +0.25 H2O: C, 71.20; H, 5.10. Found: C, 71.19; H, 4.74.

Sources & evidence

ORD record
ord-b6687a16ef9143fb9cb5c6da1a6d30a8
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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