Hydrochloric Acid → HCID 136207632, compound

HRID 1649773Notes

Reaction equation

HRID 1649773 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:35])[C:5]([CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:34]=[CH:33][C:16]([C:17]([NH:19][C@H:20]([C:28]([O:30]CC)=[O:29])[CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])=[O:18])=[CH:15][CH:14]=2)=[C:6]([NH2:8])[N:7]=1.Cl>[OH-].[Na+]>[NH2:1][C:2]1[NH:3][C:4](=[O:35])[C:5]([CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:18])=[CH:33][CH:34]=2)=[C:6]([NH2:8])[N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136120846HCID 136120846, compound

Product 1

HCID 136207632HCID 136207632, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A sample of compound 1E (0.50 g, 0.99 mmole) was stirred at 50° C. in 0.1N NaOH (18 mL) for 2 hours. The pH was adjusted to 8.0 with 1.0 N HCl and the mixture evaporated to dryness in vacuo. The resulting solid was dissolved in a minimum of ethanol/water (35% ethanol v/v) and chromatographed in 5 injections on a Regis C18 2.1 cm×50 cm, 10 micron, preparative reverse phase column. The combined fractions were reduced in vacuo to 5 mL volume and acidified with concentrated HCl to pH 3.0. Filtration gave a white solid which was dried in vacuo at 50° C. to yield the title compound, 1F, (0.185 g, 41%) as a white powder. Anal: C19H23N5O6S.3/2 H2O: C, 47.89; H, 5.48; N, 14.70. Found: C, 47.99; H, 5.51; N, 14.61. NMR (DMSO-d6) δ1.6 (t, 2H, CH2 --CH2 --CH2), 2.0 (m, 2H, --CH2 --CH2 --CO2H), 2.35 (m, 4H, CH2 --CH2 --CH2 --S and CH2 --CO2H), 2.95 (t, 2H, --CH2 --S), 4.35 (m, 1H, methine), 5.8 (br, 2H, NH2), 6.1 (br, 2H, NH2), 7.3 (d, 2H, phenyl H's ortho to sulfur), 7.75 (d, 2H, phenyl H's ortho to carbonyl), 8.55 (d, 1H, glutamic acid NH), 9.9 (br, 1H, pyrimidine NH), 12.35 (br, 2H, CO2H's).

Workup

  1. customthe mixture evaporated to dryness in vacuo
  2. dissolutionThe resulting solid was dissolved in a minimum of ethanol/water (35% ethanol v/v) and
  3. customchromatographed in 5 injections on a Regis
  4. filtrationFiltration
  5. customgave a white solid which
  6. customwas dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-6a6ce1a4b609426e81356b20fa4cf000
Source dataset
uspto-grants-1990_05
Patent number
US04921836

Reaction notes

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