Hydrochloric Acid → N-[2-(2-Nitro-benzenesulfonylamino)-ethyl]-N-[(thymin-1-yl)-acetyl]-glycine
Reaction equation
C([O:3][C:4](=[O:34])[CH2:5][N:6]([CH2:19][CH2:20][NH:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N+:31]([O-:33])=[O:32])(=[O:24])=[O:23])[C:7](=[O:18])[CH2:8][N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]1=[O:11])C.[OH-].[Li+].Cl>C1COCC1.O>[N+:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[S:22]([NH:21][CH2:20][CH2:19][N:6]([C:7](=[O:18])[CH2:8][N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]1=[O:11])[CH2:5][C:4]([OH:34])=[O:3])(=[O:24])=[O:23])([O-:33])=[O:32]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-[2-(2-Nitro-benzenesulfonylamino)-ethyl]-N-[(thymin-1-yl)-acetyl]-glycine ethyl ester (1.00 g, 2.0 mmol) in THF (10 ml,) was added a solution of lithium hydroxide (210 mg, 5 mmol) in water (10 mL) at 10° C. After stirring for 1.5 h, the reaction mixture was acidified to pH=2˜3 by adding 1 N HCl solution. The precipitated solid was filtered off, washed with water, and dried in vacuo to give the tilted product as a white solid (896 mg, 95%). 1H-NMR (500 MHz; DMSO-d6) δ 11.30 (s, 0.6H), 11.27 (s, 0.4H), 8.22˜7.85 (m, 5H), 7.31 (d, 0.6H), 7.23 (d, 0.4H), 4.63 (s, 1.2H), 4.45 (s, 0.8H), 4.19 (s, 0.8H), 4.16 (q. 0.8H), 3.93 (s, 1.2H), 3.47 (t, 1.2H), 3.34 (t, 0.8H), 3.20 (q, 1.2H), 3.04 (q. 0.8H), 1.75 (s, 3H).
Workup
- filtrationThe precipitated solid was filtered off
- washwashed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-457f0906b2d94c2ea8db2222e1a5b7b4
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022851B2
Reaction notes
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