Sodium Bicarbonate → Disodium (2R)-2-((4-acetamidophenoxy)carbonylamino)-3-sulfonatopropanoate
Reaction equation
[C:1]([NH:4][C:5]1[CH:23]=[CH:22][C:8]([O:9][C:10]([NH:12][C@@H:13]([CH2:17][S:18]([OH:21])(=[O:20])=[O:19])[C:14]([OH:16])=[O:15])=[O:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])O.[Na+:28].C(=O)(OC1C=CC([N+]([O-])=O)=CC=1)OC1C=CC(NC(=O)C)=CC=1>O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]([NH:12][C@@H:13]([CH2:17][S:18]([O-:21])(=[O:20])=[O:19])[C:14]([O-:16])=[O:15])=[O:11])=[CH:22][CH:23]=1)(=[O:3])[CH3:2].[Na+:28].[Na+:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Disodium (2R)-2-((4-acetamidophenoxy)carbonylamino)-3-sulfonatopropanoate (13) was prepared following the General Procedure for the Preparation of Alkali Metal Salts (Procedure B). (2R)-2-[(4-Acetamidophenoxy)carbonylamino]-3-sulfo-propanoic acid (13a) (83 mg, 0.24 mmol), dissolved in 2.0 mL of water, was reacted with 40.3 mg (0.48 mmol; 2.0 eq.) of sodium hydrogencarbonate (NaHCO3) dissolved in 0.5 mL of water. The mixture was sonicated with agitation for three (3) minutes, frozen, and the solvents lyophilized off to afford 88 mg (95% yield) of the title compound (13) as a colorless solid. 1H NMR (300 MHz, D2O): δ=7.21 (d, J=8.7, 2H), 6.97 (d, J=9.0, 2H), 4.36-4.32 (m, 1H), 3.28-3.22 (m, 1H), 3.12-3.04 (m, 1H), 1.96 (s, 3H) ppm. LC/MS: LC/MS (ESI): m/z=347.0 [M+H]+, 714.7 [2M+Na]+.
Workup
- customDisodium (2R)-2-((4-acetamidophenoxy)carbonylamino)-3-sulfonatopropanoate (13) was prepared
- temperaturefrozen
Sources & evidence
- ORD record
- ord-cc61f3fda4a7489b9f87db3bd2704eec
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09024055B2
Reaction notes
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