Hydrochloric Acid → HCID 22177639, compound

HRID 1797383Notes

Reaction equation

HRID 1797383 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:39])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[O:23][CH:22]3[CH:24]([N:31]4[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]4=[O:38])[O:25][CH:26]([CH2:27][N:28]=[N+:29]=[N-:30])[CH:21]3[O:20]2)=[CH:15][CH:14]=1)C.Cl>O.CCO>[N:28]([CH2:27][CH:26]1[CH:21]2[CH:22]([O:23][CH:19]([C:16]3[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:39])=[O:5])=[CH:14][CH:15]=3)[O:20]2)[CH:24]([N:31]2[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]2=[O:38])[O:25]1)=[N+:29]=[N-:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86759991HCID 86759991, compound

Product 1

HCID 22177639HCID 22177639, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (NaOH, 20.8 g, 522 mmol) in H2O (125 mL) was added to a suspension of 7 (89.8 g, 174 mmol) in EtOH (400 mL) and stirred for 4 h at room temperature. The solvent was removed and the resulting residue was diluted with H2O (300 mL). The suspension was then treated dropwise with 1M aqueous HCl (522 mmol, 522 mL) to afford a white precipitate, which was subsequently partitioned with EtOAc (1.5 L). The organic layer was then washed with H2O (2×1 L), dried (MgSO4), filtered and concentrated in vacuo to give a white foam (8, 80.2 g, 164 mmol, 95%) as a mixture of two diastereomers: 1H-NMR (400 MHz, (CD3)2SO3) δ=12.01 (s, 1H, 1H′), 11.49 (s, 1H, 1H′), 7.78 (d, J=8.0, 1H), 7.74 (d, J=8.0, 1H′), 7.43 (d, J=8.5, 2H), 7.37 (d, J 8.5, 2H′), 6.96 (d, J=8.5, 2H), 6.93 (d, J=8.5, 2H′), 6.07 (s, 1H′), 5.93 (s, 1H), 5.91 (s, 1H, 1H′), 5.67 (d, J=8.0, 1H), 5.66 (d, J=8.0, 1H′), 5.20-4.81 (m, 2H, 2H′), 4.31 (m, 1H, 1H′), 3.96 (m, 2H, 2H′), 3.62 (m, 2H, 2H′), 2.22 (m, 2H, 2H′), 1.70 (m, 2H, 2H′), 1.54 (m, 2H, 2H′), 1.41 (m, 2H, 2H′); 13C-NMR (400 MHz, (CD3)2SO3) δ=175.3, 175.3, 164.1, 164.0, 160.7, 160.6, 151.2, 151.2, 144.3, 143.7, 129.3 (2C), 129.3 (2C), 128.6, 128.6, 115.1 (2C), 115.0 (2C), 107.6, 103.5, 103.1, 102.8, 93.5, 92.5, 85.9, 85.1, 83.2, 82.8, 82.6, 81.5, 68.3, 68.3, 52.7, 52.5, 34.5, 34.5, 29.2, 29.1, 26.0, 25.9, 25.1, 25.1; IR (film) ν=3354, 3183, 2941, 2101, 1684, 1245, 1069, 1050, 1023, 995, 824; HRMS (MALDI-FTMS) mn/z 510.1600 (510.1595 calculated for C22H25N5O8Na (M+Na)+).

Workup

  1. customThe solvent was removed
  2. additionthe resulting residue was diluted with H2O (300 mL)
  3. customto afford a white precipitate, which
  4. customwas subsequently partitioned with EtOAc (1.5 L)
  5. washThe organic layer was then washed with H2O (2×1 L)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a white foam (8, 80.2 g, 164 mmol, 95%)
  10. additionas a mixture of two diastereomers

Sources & evidence

ORD record
ord-729acf416ad04542a48dff78b76a6693
Source dataset
uspto-grants-2006_04
Patent number
US07034147B2

Reaction notes

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