Sulfuric Acid → HCID 136383512, compound

HRID 2110605Notes

Reaction equation

HRID 2110605 reaction equation
[CH3:1][C:2]([CH3:39])([CH3:38])[CH2:3][CH2:4][C:5]1(O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26]C(=O)OC(C)(C)C)=[CH:25][C:19]=3[S:18](=[O:35])(=[O:34])[N:17]=2)[C:6]1=[O:36].[OH:40]S(O)(=O)=O.[C:45](#[N:47])[CH3:46]>>[NH2:26][C:24]1[CH:23]=[CH:22][C:20]2[NH:21][C:16]([C:7]3[C:6](=[O:36])[C:5]([NH:47][C:45](=[O:40])[CH3:46])([CH2:4][CH2:3][C:2]([CH3:38])([CH3:39])[CH3:1])[C:14]4[C:9]([C:8]=3[OH:15])=[CH:10][CH:11]=[CH:12][CH:13]=4)=[N:17][S:18](=[O:35])(=[O:34])[C:19]=2[CH:25]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 136383513HCID 136383513, compound

Product 1

HCID 136383512HCID 136383512, compoundYield 92%

Procedure

To a suspension of the product of Example 74C (1.0 g, 1.8 mmol) in acetonitrile (16 mL) at 0° C. was added conc. H2SO4 (8 mL). The reaction mixture was warmed to room temperature and stirred for 2 h. The solution was poured unto ice (100 g) and extracted with 3:1 dichloromethane:isopropanol (3×50 mL). The organic extracts were combined, dried (Na2SO4), and concentrated in vacuo. The resulting residue was dried under high vacuum to give the title compound as a yellow solid (0.98g, 92%). 1H NMR (300 MHz, DMSO-d6), δ ppm 0.39-0.56 (m, 1H), 0.65 (s, 9H), 0.81-0.98 (m, 1H), 1.77-1.90 (m, 4H), 1.92-2.07 (m, 1H), 6.90-7.04 (m, 2H), 7.39-7.58 (m, 3H), 7.73 (t, J=7.54 Hz, 1H), 8.11 (d, J=7.35 Hz, 1H), 9.16 (s, 1H), 13.38 (s, 1H); MS m/z 497.2 (M+H)+.

Workup

  1. extractionextracted with 3:1 dichloromethane
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was dried under high vacuum

Sources & evidence

ORD record
ord-e48b9b17bea245abb62864c29a09d2e2
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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