Acetic Acid → HCID 68493021, compound

HRID 643824Notes

Reaction equation

HRID 643824 reaction equation
C([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])C.[Li+].[OH-].CC(O)=O.C1(C)C=CC=CC=1>C1COCC1.CO>[CH3:31][O:30][C:26]1[CH:25]=[C:24]2[C:29]([C:20]([O:19][C@H:17]3[CH2:16][NH:15][C@H:14]([C:12]([NH:11][C@:6]4([C:4]([OH:5])=[O:3])[CH2:8][C@H:7]4[CH:9]=[CH2:10])=[O:13])[CH2:18]3)=[CH:21][C:22]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[N:23]2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 3939Lithium HydroxideHCID 207653161-{[4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 68493021HCID 68493021, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of compound 6 (0.067 mmol) in THF-MeOH 2:3 (2 ml) was added 1M LiOH 10 equiv. The solution was kept at 50° C. for 2.5 hrs. After cooling to RT, HOAc 20 eq. was added followed by toluene (2 ml) and then concentrated to dryness. The residue was taken up in DCM and filtered form the salts which gave the title compound (0.07 mmol). Purity >95% by HPLC M+H+ 474.

Workup

  1. concentrationconcentrated to dryness
  2. filtrationfiltered form the salts which

Sources & evidence

ORD record
ord-b38640082de94532bb937d0237cc7c65
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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