Sodium Hydroxide → N-(Carboxymethyl)-N-[2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-5-[(12-phenoxydodecyl)oxy]phenyl]glycine
Reaction equation
C[O:2][C:3](=[O:49])[CH2:4][N:5]([C:11]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:14]=[C:13](OCCOCCOCCOCC)[CH:12]=1)[CH2:6][C:7]([O:9]C)=[O:8].[OH-].[Na+].C(CN(C1C=C(OCCCCCCCCCCCCOC2C=CC=CC=2)C=[C:63]([O:87][CH2:88][CH2:89][O:90][CH2:91][CH2:92][O:93][CH2:94][CH2:95][O:96]CC)[CH:62]=1)CC(O)=O)(O)=O>CO.O1CCOCC1>[C:7]([CH2:6][N:5]([C:11]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:14]=[CH:13][C:12]=1[O:96][CH2:95][CH2:94][O:93][CH2:92][CH2:91][O:90][CH2:89][CH2:88][O:87][CH2:63][CH3:62])[CH2:4][C:3]([OH:2])=[O:49])([OH:9])=[O:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1.15 g (1.67 mmol) of N-[3-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-5-[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester and 1.4 ml (8.4 mmol) of 6 N NaOH in 50 ml of methanol and 10 ml of dioxane was stirred at reflux under argon for 19 hours. After the usual workup the product was crystallized from acetone-hexane to give 0.94 g (85% yield), mp 58°-61°, of N-(carboxymethyl)-N-[3-[2-[2-(2-ethoxyethoxy)-ethoxy]ethoxy]-5-[(12-phenoxydodecyl)oxy]phenyl]glycine.
Workup
- temperatureat reflux under argon for 19 hours
- customAfter the usual workup the product was crystallized from acetone-hexane
- customto give 0.94 g (85% yield), mp 58°-61°
Sources & evidence
- ORD record
- ord-fe54a0c0e4d24a0fb1efd1988e770b02
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05324747
Reaction notes
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