Hydrochloric Acid → HCID 10097843, compound

HRID 1815480Notes

Reaction equation

HRID 1815480 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([C:28]([O:30]CC)=[O:29])=[O:27])[CH2:22][CH2:21]2)=[O:19])=[CH:12][C:11]=1[N+:33]([O-:35])=[O:34].[Li+].[OH-].O.Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([C:28]([OH:30])=[O:29])=[O:27])[CH2:22][CH2:21]2)=[O:19])=[CH:12][C:11]=1[N+:33]([O-:35])=[O:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 86592885HCID 86592885, compound

Product 1

HCID 10097843HCID 10097843, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of the ethyl ester (40 mg, 0.074 mmol) from Example 43A in 2 mL of ethanol was added saturated LiOH (0.25 mL). The mixture was then stirred at room temperature for 2 hours. Water (2 mL) was then added to the reaction mixture, which was then acidified to pH=2 with concentrated HCl. The precipitates were collected through filtration, washed with cold water, dried under vacuum to give the title compound (30 mg, 79%) as a light yellow solid. 1H NMR (d6-DMSO, 300 MHz) δ 3.52 (br m, 4H), 3.62 (br m, 2H), 3.76 (br m, 2H), 6.84 (d, J=9.0 Hz, 1H), 7.46 (d, J=15.3 Hz,1H), 7.56 (d, J=15.3 Hz, 1H), 7.63 (dd, J=2.7, 8.7 Hz, 1H), 7.83 (d, J=9.0 Hz, 1H), 7.93 (d, J=9.0 Hz, 1H), 7.96 (d, J=2.7 Hz, 1H), 8.70 (br d, 1H). MS (APCI) (M-COO)+ at m/z 466, 468, 470.

Workup

  1. filtrationThe precipitates were collected through filtration
  2. washwashed with cold water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a271aff82b174cb4ad0feb8652ecc283
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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