Hydrochloric Acid → N-{[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine

HRID 1794945Notes

Reaction equation

HRID 1794945 reaction equation
C([O:3][C:4](=[O:49])[CH2:5][N:6]([C:22](=[O:48])[CH2:23][N:24]1[CH:47]=[CH:46][C:28]([NH:29][C:30]([O:32][CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[N:27][C:25]1=[O:26])[CH2:7][CH2:8][NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])C.[OH-].[Li+].Cl.[Cl-].[Na+]>C1COCC1.O>[CH:33]([O:32][C:30]([NH:29][C:28]1[CH:46]=[CH:47][N:24]([CH2:23][C:22]([N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])(=[O:11])=[O:12])[CH2:5][C:4]([OH:49])=[O:3])=[O:48])[C:25](=[O:26])[N:27]=1)=[O:31])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 5234Sodium ChlorideHCID 22222376N-{[4-N-(Benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester

Product 1

HCID 22222393N-{[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycineYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{[4-N-(Benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester (1.91 g, 2.75 mmol) in THF (10 mL) was added a solution of lithium hydroxide (290 mg, 6.9 mmol) in water (9 mL) at 10° C. After stirring for 1.5 h, the reaction mixture was acidified to pH=3˜4 by adding 1 N HCl solution. The aqueous layer was saturated with sodium chloride and organic layer was separated. The aqueous layer was extracted with THF (15 mL×2). The combined organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated and triturated with ethyl alcohol to precipitate solid. The precipitated solid was filtered off, washed with water, and dried in vacuo to give the tilted product as a white solid (1.42 g, 78%). 1H-NMR (500 MHz; DMSO-d6) δ 8.25˜7.80 (m, 5H), 7.50˜7.25 (m, 10H), 6.94 (d, 0.6H), 6.92 (d, 0.4H), 6.79 (1H, s), 4.78 (s, 1.2H), 4.60 (s, 0.8H), 4.22 (s, 0.8H), 3.94 (s, 1.2H), 3.50 (t, 1.2H), 3.35 (t, 0.8H), 3.24 (q, 1.2H), 3.02 (q, 0.8H).

Workup

  1. customwas separated
  2. extractionThe aqueous layer was extracted with THF (15 mL×2)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customtriturated with ethyl alcohol
  7. customto precipitate solid
  8. filtrationThe precipitated solid was filtered off
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-fabdec24943d40c3a1d4e6e326d388f3
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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