Hydrochloric Acid → HCID 21868368, compound

HRID 1064614Notes

Reaction equation

HRID 1064614 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][N:6]1[CH:26]=[CH:25][C:10]([NH:11][C:12]([O:14][CH2:15][C:16]2[CH:24]=[CH:23][C:22]3[O:21][CH2:20][O:19][C:18]=3[CH:17]=2)=[O:13])=[N:9][C:7]1=[O:8])C.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH2:15]([O:14][C:12]([NH:11][C:10]1[CH:25]=[CH:26][N:6]([CH2:5][C:4]([OH:27])=[O:3])[C:7](=[O:8])[N:9]=1)=[O:13])[C:16]1[CH:24]=[CH:23][C:22]2[O:21][CH2:20][O:19][C:18]=2[CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68524231[4-N-(Piperonyloxycarbonyl)-cytosin-1-yl]-acetic acid ethyl ester

Product 1

HCID 21868368HCID 21868368, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of [4-N-(piperonyloxycarbonyl)-cytosin-1-yl]-acetic acid ethyl ester (6.40 g, 17 mmol) in tetrahydrofuran (30 mL) and water (60 mL) was added lithium hydroxide monohydrate (1.6 g) at room temperature. After stirring 20 min, the reaction mixture was acidified by adding 1 N HCl (40 mL). The precipitated solid was filtered off, washed with water (20 mL) and ethyl alcohol (20 mL), and dried in vacuo to give the desired product (5.8 g, 98%). 1H-NMR (500 MHz; DMSO-d6) δ 7.94 (d, 1H), 6.93 (d, 1H), 6.90 (s, 1H), 6.82 (s, 2H), 5.93 (s, 2H), 4.99 (s, 2H), 4.43 (s, 2H).

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed with water (20 mL) and ethyl alcohol (20 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5500eca0a87e4374a1b6373c8fdb0f35
Source dataset
uspto-grants-2005_11
Patent number
US06969766B2

Reaction notes

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