Hydrochloric Acid → 5-[(N-Methyl-N-butylamino)carbonyl]-2,4-bisbenzyloxybenzoic acid

HRID 1927698Notes

Reaction equation

[CH3:1][N:2]([C:7]([C:9]1[C:10]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:11][C:12]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:13]([CH:18]=1)[C:14]([O:16]C)=[O:15])=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Li+].Cl>C1COCC1.O.CO.C(OCC)C>[CH3:1][N:2]([C:7]([C:9]1[C:10]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:11][C:12]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:13]([CH:18]=1)[C:14]([OH:16])=[O:15])=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 22 °C

Procedure

59 g (127.8 mmol) of methyl 5-[(N-methyl-N-butylamino)carbonyl]-2,4-bisbenzyloxybenzoate are dissolved in 200 ml of THF and added to a solution of 100 g (4.2 mol) of lithium hydroxide in 300 ml of water and 150 ml of methanol. The mixture is stirred for 12 h at 22° C., diluted with 250 ml of diethyl ether and acidified using 1N hydrochloric acid. The organic phase is separated off and washed a further three times with 100 ml of N hydrochloric acid each time, dried over sodium sulfate and evaporated. The crude product obtained in this way (80 g) is crystallised from ethyl acetate: 33 g (57.7%) of 5-[(N-methyl-N-butylamino)carbonyl]-2,4-bisbenzyloxybenzoic acid (white crystals); MW 447.5;

Workup

customThe organic phase is separated off
washwashed a further three times with 100 ml of N hydrochloric acid each time
dry with materialdried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-088ff8a45a754a84b2c0a5db81885cac
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183279B2

Reaction notes

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