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

HRID 546335

반응식

HRID 546335 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(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.

후처리

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

출처 및 근거

ORD 기록
ord-848b56a50cf74721a64e14d6dee48019
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935841B2

연결된 노트

불러오는 중…