Sulfamic Acid → HCID 21106512, compound

HRID 1783674Notes

Reaction equation

HRID 1783674 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:13])=[CH:11][C:10]([N:14]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:15]2[C:24]3[C:19](=[CH:20][C:21]([CH2:25][OH:26])=[CH:22][CH:23]=3)[C:18](=[O:27])[N:17]([CH:28]([CH3:30])[CH3:29])[N:16]=2)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I(C1C=CC=CC=1C(O)=O)(=O)=[O:39].S(=O)(=O)(O)N.Cl([O-])=O.[Na+]>CS(C)=O.C(Cl)Cl.O>[C:34]([O:33][C:31]([N:14]([C:10]1[CH:11]=[C:12]([CH3:13])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[N:9]=1)[C:15]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([OH:39])=[O:26])=[CH:22][CH:23]=2)[C:18](=[O:27])[N:17]([CH:28]([CH3:29])[CH3:30])[N:16]=1)=[O:32])([CH3:35])([CH3:37])[CH3:36]

Participants

8

Reactant 4

HCID 5987Sulfamic AcidHCID 1087942-Iodoxybenzoic acidHCID 23668197Sodium ChloriteHCID 68897255HCID 68897255, compound

Product 1

HCID 21106512HCID 21106512, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-[tert-Butoxycarbonyl-(6-hydroxymethyl-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-1-yl)-amino]-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.2 g, 0.39 mmol) was dissolved in DMSO (3 ml). To this was added 2-iodoxybenzoic acid (IBX) (0.22 g, 0.78 mmol) in one portion and the reaction mixture was stirred at RT for 24 hours. After this time, the reaction mixture was partitioned between EtOAc (20 ml) and water (20 ml), the organic layer was separated and washed with water (3×20 ml) before being dried (MgSO4), filtered and concentrated under vacuum. The resulting orange oil (0.197 g, 0.38 mmol) was dissolved in DCM (3 ml) and water (3 ml). To this was added sulfamic acid (0.037 g, 0.38 mmol) and the reaction mixture was stirred vigorously at 0° C. After 5 min, sodium chlorite (0.034 g, 0.38 mmol) was added in one portion and the mixture stirred for a further hour. After this time, the reaction mixture was diluted with DCM (20 ml) and washed with water (10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was purified by flash column chromatography (elution: 50% heptane, 50% EtOAc to 100% EtOAc) to give the title compound (0.088 g, 44% yield) as a white solid. MS (ESI+)=(M+H)+ 528.41.

Workup

  1. customAfter this time, the reaction mixture was partitioned between EtOAc (20 ml) and water (20 ml)
  2. customthe organic layer was separated
  3. washwashed with water (3×20 ml)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. stirringthe reaction mixture was stirred vigorously at 0° C
  8. waitAfter 5 min
  9. stirringthe mixture stirred for a further hour
  10. washwashed with water (10 ml)
  11. customThe organic layer was separated
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. concentrationconcentrated under vacuum
  15. customThe resulting residue was purified by flash column chromatography (elution: 50% heptane, 50% EtOAc to 100% EtOAc)

Sources & evidence

ORD record
ord-e7325eba3805489c9300d96143e6601c
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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