Trifluoroacetic acid → HCID 86707254, compound

HRID 2199965Notes

Reaction equation

HRID 2199965 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:15]([OH:17])=[O:16])[CH:12]=2)[CH:7]([CH3:18])[CH2:6]1.FC(F)(F)C(O)=O.CC1C=CC=C(C)C=1CN1C2C(=CC=C(CC(O)=O)C=2)[C@H](C)C1>CCCCCC.C(O)(C)C>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:15]([OH:17])=[O:16])[CH:12]=2)[C@@H:7]([CH3:18])[CH2:6]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 60152011HCID 60152011, compoundHCID 86707255HCID 86707255, compound

Product 1

HCID 86707254HCID 86707254, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 21585144Isopropanol hexaneSolvent

Procedure

The compound [78] obtained in Example 78 (26 mg) was optically resolved by chiral column chromatography (CHIRALCEL (registered trademark) OD (CHRALCEL OD) manufactured by Daicel Corporation, 2 cm×25 cm; 0.1% trifluoroacetic acid, hexane/isopropyl alcohol=85/15; flow rate 20 mL/min). (3R*)-2-[1-(2,6-dimethylbenzyl)-2,3-dihydro-3-methyl-1H-indole-6-yl]acetic acid [79A] (15 mg) as a pale brown solid was obtained from the preceding fraction (retention time: 5.3 minutes), and (3S*)-2-[1-(2,6-dimethylbenzyl)-2,3-dihydro-3-methyl-1H-indole-6-yl]acetic acid [79B] of the same (16 mg) as a pale brown solid was obtained from the posterior fraction (retention time: 10.8 minutes). (Both of them were un-identified, and thus one of them was referred to as 3R*, and the other one as 3S* for convenience.)

Sources & evidence

ORD record
ord-8cdf23372339446cbd95381d8053e389
Source dataset
uspto-grants-2016_06
Patent number
US09359350B2

Reaction notes

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