Phosphoric Acid → HCID 53248042, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[S:15](Cl)(=[O:18])(=[O:17])[OH:16].C(N(C(C)C)C(C)C)C.C([O-])([O-])=O.[Na+].[Na+].OP(O)(O)=O>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][CH:11]([S:15]([OH:18])(=[O:17])=[O:16])[C:12]([OH:14])=[O:13]Participants
Conditions
- Temperature
- 75 °C
Procedure
Alternative procedure: 4-(pyridin-2-yldisulfanyl)butanoic acid (106 mg, 0.462 mmol) was coevaporated with 1,2-dichloreoethane (2×5 ml), redisolved in 5 ml of 1,2-dichloreoethane and placed in a preheated 75° C. oil bath. To this solution, sulfurochloridic acid (154 μL, 2.311 mmol) and N-ethyl-N-isopropylpropan-2-amine (161 μL, 0.924 mmol) were added. The mixture was placed in the pre-heated 75° C. oil bath for 45 min. Another portion of sulfurochloridic acid (45 μL, 0.675 mmol) was added and the reaction was heated at 75° C. for 1 more hour until the reaction was completed (monitored by HPLC). To the mixture was added concentrated Na2CO3 until pH 11. The resulting mixture was stirred for 10 min, neutralized with H3PO4 to pH 7.5 and concentrated. The crude product was purified by HPLC on a C-18 column eluting with a gradient of 100% of water (0.5% HAc) to 80% water (0.5% HAc)/20% of MeOH to afford 4-(pyridin-2-yldisulfanyl)-2-sulfobutanoic acid (63 mg, 0.204 mmol, 44.1% yield).
Workup
- customplaced in a preheated 75° C.
- concentrationconcentrated
- customThe crude product was purified by HPLC on a C-18 column
- washeluting with a gradient of 100% of water (0.5% HAc) to 80% water (0.5% HAc)/20% of MeOH
Sources & evidence
- ORD record
- ord-3b0f3c198fe046b795e9cfd4abe5f4a5
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598362B2
Reaction notes
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