Isopropanol → 2-[3-(S)-[3-(2-(7-Chloro-2-quinolinyl)(E/Z)ethenyl)phenyl]-3-hydroxypropyl]benzoic acid methyl ester

HRID 414888

Reaction equation

HRID 414888 reaction equation
Cl.N(CCO)(CCO)CCO.[O-]S([O-])(=O)=O.[Mg+2].[CH3:18][O:19][C:20](=[O:50])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=[CH:38][C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][C:43]([Cl:49])=[CH:44][CH:45]=3)[N:40]=2)[CH:32]=1)=[O:30].CC(O)C>C1(C)C=CC=CC=1>[CH3:18][O:19][C:20](=[O:50])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28][C@@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=[CH:38][C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][C:43]([Cl:49])=[CH:44][CH:45]=3)[N:40]=2)[CH:32]=1)[OH:30]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 101814Triethanolamine hydrochlorideHCID 53394881Methyl 2-(3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-oxopropyl)benzoate

Product 1

HCID 540063032-[3-(S)-[3-(2-(7-Chloro-2-quinolinyl)(E/Z)ethenyl)phenyl]-3-hydroxypropyl]benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a jacketed 2-L 3-neck flask under nitrogen with jacket temperature set at 51° C. via an external heat exchanger and equipped with internal thermometer and mechanical stirrer at 250 rpm was added 300 mL 100 mM pH 8.0 triethanolamine-HCl, 0.6 mL 1 M MgSO4, 3.0 g of SEQ ID NO:20 catalyst as prepared in Example 3, 0.1 g NADP-Na2, to give a pale yellow solution. After stirring for 10 minutes, 100 g 2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-ketopropyl]benzoic acid methyl ester was added portion-wise over ˜5 minutes. To the slurry was added 500 mL (390 g) of IPA and 100 mL (85 g) toluene. The progress of the reaction was monitored by achiral HPLC as described in Example 4 and 6. The procedure as described in Example 9 was used for sampling and sample prep.

Workup

  1. customTo a jacketed 2-L 3-neck flask under nitrogen with jacket temperature set at 51° C. via an external heat exchanger
  2. customequipped with internal thermometer and mechanical stirrer at 250 rpm
  3. customto give a pale yellow solution
  4. aliquotfor sampling

Sources & evidence

ORD record
ord-1332fbc3fc7343d3ae3f4f9848ebc0f4
Source dataset
uspto-grants-2012_01
Patent number
US08088610B2

Linked notes

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