Sulfamic Acid → HCID 19066366, compound

HRID 1289227Notes

Reaction equation

HRID 1289227 reaction equation
Cl([O-])=O.[Na+].S(=O)(=O)(O)N.[F:10][C:11]1[CH:18]=[C:17]([N:19]([CH:23]2[C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][C:26]=3[CH2:25][CH2:24]2)[N:33]=[C:32]([CH3:36])[N:31]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C:30]4=[O:45])[CH2:20][C:21]#[CH:22])[CH:16]=[CH:15][C:12]=1[CH:13]=[O:14].C([O-])(=[O:48])C.[Na+]>C(O)(=O)C.C(O)(C)(C)C>[F:10][C:11]1[CH:18]=[C:17]([N:19]([CH:23]2[C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][C:26]=3[CH2:25][CH2:24]2)[N:33]=[C:32]([CH3:36])[N:31]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:41])([CH3:43])[CH3:42])[C:30]4=[O:45])[CH2:20][C:21]#[CH:22])[CH:16]=[CH:15][C:12]=1[C:13]([OH:48])=[O:14]

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 517045Sodium AcetateHCID 18925200HCID 18925200, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 19066366HCID 19066366, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6386tert-ButanolSolvent

Procedure

Sodium chlorite (0.28 g) and sulphamic acid (0.24 g) were added portionwise to a stirred mixture of o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzaldehyde (0.47 g), 0.2M sodium acetate in acetic acid buffer (pH 4, 70 ml) and tert-butanol (70 ml). The mixture was stirred at ambient temperature for 24 hours. The mixture was partitioned between methylene chloride and a saturated aqueous sodium dihydrogen phosphate solution. The organic phase was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography to give o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzoic acid (0.41 g);

Workup

  1. customThe mixture was partitioned between methylene chloride
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-de296b32892d4b8ba249198dc3c78e3f
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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