Isopropanol → HCID 145857632, compound

HRID 723034Notes

Reaction equation

HRID 723034 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]([C:10]1[S:11][C:12]([S:33][CH3:34])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[C:28]([CH2:30][OH:31])[CH:27]=[CH:26][C:25]=3[CH3:32])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(O)(C)C.CCOC(C)=O>CS(C)=O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]([C:10]1[S:11][C:12]([S:33][CH3:34])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[C:28]([CH:30]=[O:31])[CH:27]=[CH:26][C:25]=3[CH3:32])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 145857611HCID 145857611, compound

Product 1

HCID 145857632HCID 145857632, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The {[4-(5′-hydroxymethyl-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 7: step b) 30 mg, 0.056 mmol) was dissolved in a mixture of DMSO (1 mL) and DCM (1 mL) and cooled to 0° C. Triethylamine (12 μL, 0.084 mmol) and sulfur trioxide-pyridine complex (11 mg, 0.068 mmol) were added and the solution was stirred for 1 h at 0° C. Partial conversion was evident by TLC. Additional triethylamine (20 μL, 0.14 μL) and sulfur trioxide-pyridine complex (18 mg, 0.11 mmol) were added and the solution was stirred for 3 h at rt. Isopropanol (250 μL) was added, the reaction was stirred for 15 min, and EtOAc (40 mL) was added. The EtOAc solution was extracted with citric acid (2×10 mL), NaHCO3 (2×10 mL), water (5×10 mL), and brine (20 mL), and was dried over sodium sulfate. Removal of the solvent in vacuo yielded the title compound (26 mg, 87%) which was used without further purification. 1H-NMR (CD3OD): δ 10.00 (s, 1H), 7.99 (m, 3H), 7.81 (dd, 1H, J=1.6 7.7 Hz), 7.72 (d, 1H, J=7.7 Hz), 7.59 (m, 2H), 7.46 (d, 1H, J=7.7 Hz), 2.58 (s, 3H), 2.30 (s, 3H), 1.51 (s, 9H).

Workup

  1. stirringthe solution was stirred for 3 h at rt
  2. stirringthe reaction was stirred for 15 min
  3. extractionThe EtOAc solution was extracted with citric acid (2×10 mL), NaHCO3 (2×10 mL), water (5×10 mL), and brine (20 mL)
  4. dry with materialwas dried over sodium sulfate
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-c7a8d733c21c48e387549e1179fc5127
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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