Carbon Dioxide → (2R)-2-methyl-3-phenylpropanoic acid

HRID 546335

反応式

HRID 546335 の反応式
C(N)(C)(C)C.[CH3:6][C@@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9].C(=O)=O.C1(/C(=C\C2C=CC=CC=2)/C(O)=O)C=CC=CC=1>CO>[CH3:6][C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9]

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 700620alpha-Phenylcinnamic acid, (E)-HCID 24786872(s)-2-Methyl-3-phenylpropionic acid tert-butylamine salt

生成物 1

HCID 5287791(2R)-2-methyl-3-phenylpropanoic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(S)-2-Methyl-3-phenylpropionic acid tert-butylamine salt, reaction time 40 minutes, conversion 100%, ee 96.5% (SFC, 2× Chiralpak AD-H columns, 10% methanol, 3000 psi CO2, 35° C., flow rate 3 ml/minute, retention times R 7.1 minutes, S 7.7 minutes, (E)-phenylcinnamic acid 12 minutes). The free acid was liberated by partitioning between dichloromethane and 2M HCl. The organic layer was dried (Na2SO4), filtered and the solvent was evaporated to give (R)-2-Methyl-3-phenylpropionic acid as a pale yellow solid. [α]D20+98.6, c=2.03, CHCl3. [α]D20+100.6, c=0.54, acetone. [α]D20+103.5 (c=1.00, MeOH). Lit. (M. B. Watson and G. W. Youngson, J. Chem. Soc. C, 1968, 258-261; +140.8, c=2.04, CHCl3). 1H NMR analysis of the (S)-methyl mandelate (E. Tyrell, M. W. H. Tang, G. A. Skinner and J. Fawcett, Tetrahedron, 1996, 52, 9841-9852) confirmed assignment of (S)-configuration.

後処理

  1. customby partitioning between dichloromethane and 2M HCl
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-848b56a50cf74721a64e14d6dee48019
出典データセット
uspto-grants-2011_05
特許番号
US07935841B2

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