Water → HCID 131714714, compound

HRID 246836Notes

Reaction equation

HRID 246836 reaction equation
[CH2:1](S(Cl)(=O)=O)[CH2:2][CH2:3][CH3:4].CO[C:11]1[N:12]=[C:13]([O:20][C:21]2[CH:26]=[CH:25][C:24]([N+]([O-])=O)=[CH:23][CH:22]=2)[N:14](C)[S:15](=[O:18])(=[O:17])[N:16]=1.C(N([CH2:35][CH3:36])CC)C.[OH2:37].[CH2:38]1[CH2:42]O[CH2:40][CH2:39]1>>[C:13]([NH:12][C:11](=[N:16][S:15](=[O:18])(=[O:17])[NH:14][CH2:1][CH2:2][CH2:3][CH3:4])[C:36]1[CH:35]=[CH:40][CH:39]=[CH:38][CH:42]=1)([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:37]

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 12785931HCID 12785931, compound

Product 1

HCID 131714714HCID 131714714, compound

Procedure

n-Butylsulfonoyl chloride (6.67 g) in THF (50 ml) is added dropwise to a stirred solution of the carbamate compound of Step 1. above (95 g) and triethylamine (4 g) in THF (160 ml) cooled to -78° C. The reaction mixture is warmed to RT, stirred overnight, poured into H2O and extracted with diethyl ether. The diethyl ether extract is washed, dried, filtered and evaporated, and the residue flash chromatographed (silica gel) affording the desired product in purified form.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe diethyl ether extract
  3. washis washed
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue flash chromatographed (silica gel)

Sources & evidence

ORD record
ord-cdf80663dfad4ef98d9f1c0c5eea6919
Source dataset
uspto-grants-1987_11
Patent number
US04704388

Reaction notes

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