phenylalaninol, (S)- → 215122-74-0

HRID 2214854Notes

Reaction equation

HRID 2214854 reaction equation
[Cl:1][C:2]1[C:3]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:4][C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:18]=1.N[C@@H](CC1C=CC=CC=1)CO>CCCCCCC>[Cl:1][C:2]1[C:3]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:4][C:5]2[O:10][C@H:9]([C:11]([F:13])([F:12])[F:14])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 447213phenylalaninol, (S)-HCID 9905741HCID 9905741, compound

Product 1

HCID 9858913215122-74-0Yield 33.3%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

To a solution of 6-chloro-7-(1,1-dimethylethyl)-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid (Example 8)(11.4 g, 34.1 mmol) and (S)-(−)-2-amino-3-phenyl-1-propanol (2.57 g, 17.00 mmol) was added n-heptane (200 mL) and the mixture set aside for 16 h. The resulting suspension was filtered yielding a solid (3.8 g). This solid was recrystallized from 2-butanone (20 mL) and n-heptane (200 mL) yielding upon filtration a white solid (3.0 g). This solid was dissolved in ethyl acetate (100 mL) and washed with 1 N hydrochloric acid (50 mL) and brine (2×50 mL), dried over MgSO4 and concentrated in vacuo yielding a white solid. This solid was recrystallized from n-heptane yielding the title compound of high optical purity as a crystalline solid(1.7 g, 30%): mp 175.4–176.9° C. 1H NMR (acetone-d6/300 MHz) 7.86 (s, 1H), 7.52 (s, 1H), 7.12 (s, 1H), 5.83 (q, 1H, J=7.1 Hz), 1.48 (s, 9H). Anal. Calc'd for C15H14O3F3Cl: C, 53.83; H, 4.22; N, 0.0; Cl, 10.59. Found: C, 53.78; H, 4.20; N, 0.0; Cl, 10.65. This compound was determined to have an optical purity of greater than 90% ee. Chiral purity was determined as describe in Example 66.

Workup

  1. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-47d242fab35f43ccb35bbb4afde9faf9
Source dataset
uspto-grants-2006_09
Patent number
US07109211B2

Reaction notes

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