Water → 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-(cyclopropylmethoxy)phenyl)acetic acid
Reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH2:24][C:25]([O:27]C)=[O:26])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH:21]1[CH2:23][CH2:22]1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[Li+].[OH-]>C1COCC1>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH2:24][C:25]([OH:27])=[O:26])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH:21]1[CH2:22][CH2:23]1)[S:9]([CH3:12])(=[O:10])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-(cyclopropylmethoxy)phenyl)acetate (1.2 g, 2.90 mmol) in THF:water=1:1 (35 ml), LiOH (0.695 g, 29.0 mmol) was added, and the mixture was reacted for 30 minutes at RT. THF was evaporated, and the aqueous residue was acidified with HCl 6N (pH=7). The mixture was extracted with EtOAc (3×), and the combined organic layers were dried over Na2SO4. The solvent was removed under vacuum affording 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-(cyclopropylmethoxy)phenyl)acetic acid (1.1 g, 2.75 mmol, 95% yield, MS/ESI+ 400.0 [MH]+). This intermediate was used without any additional purification.
Workup
- customthe mixture was reacted for 30 minutes at RT
- customTHF was evaporated
- extractionThe mixture was extracted with EtOAc (3×)
- dry with materialthe combined organic layers were dried over Na2SO4
- customThe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-73aef233ab1440ffb53c1b260de60261
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09265768B2
Reaction notes
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