Hydrochloric Acid → {[4-(4-Fluoro-butoxy)benzenesulfonyl](4-methoxy-benzyl)-amino}-acetic acid

HRID 1662982Notes

Reaction equation

C[O:2][C:3](=[O:30])[CH2:4][N:5]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][F:29])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.Cl>C1COCC1.CO.O>[F:29][CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([N:5]([CH2:4][C:3]([OH:30])=[O:2])[CH2:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

To a solution of 1.04 g (2.37 mmol) of ([4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxybenzyl)-amino)-acetic acid methyl ester in 15 ml of THF, 15 ml of MeOH and 7 ml of H2O, 0.24 g (5.7 mmol) of LiOH mono-hydrate is added in portions and the mixture is stirred for 30 min at 0-5° C. After stirring for additional 3.5 h, the reaction mixture is acidified with 1N aqueous HCl and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure to give {[4-(4-fluoro-butoxy)benzenesulfonyl](4-methoxy-benzyl)-amino}-acetic acid; NMR (CDCl3): 1.86-1.96 (m, 4H), 3.79 (s, 3H), 3.90 (s, 2H), 4.08 (t, 2H, J=5.52 Hz), 4.38 (s, 2H), 4.48 (t, 1H, J=6.04 Hz), 4.55-4.65 (m, 1H), 6.84 (d, 2H, J=8.56 Hz), 6.98 (d, 2H, J=9.08 Hz), 7.14 (d, 2H, J=8.56 Hz), 7.81 (d, 2H, J=9.08 Hz).

Workup

stirringAfter stirring for additional 3.5 h
extractionextracted with AcOEt
washThe combined extracts are washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6eaeaec9885e46c397df8186acbc5847
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034810B2

Reaction notes

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