4-Nitrobenzenesulfonyl chloride → HCID 70196558, compound

HRID 456262Notes

Reaction equation

HRID 456262 reaction equation
[NH2:1][C@H:2]1[C@H:6]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:5][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O>[OH:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C@H:2]([NH:1][S:27]([C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:26][CH:25]=2)(=[O:28])=[O:29])[CH2:3][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 67776146HCID 67776146, compound

Product 1

HCID 70196558HCID 70196558, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of (3S*,4R*)-tert-butyl 3-amino-4-(3-hydroxypropyl)pyrrolidine-1-carboxylate (0.55 g, 2.25 mmol) and p-nitrophenylsulfonyl chloride (0.50 g, 2.25 mmol) and Na2CO3 (0.29 g, 2.70 mmol) in 8 mL THF-water, 3:1, was stirred overnight at room temperature. THF was evaporated, the mixture was diluted with H2O, extracted with CH2Cl2, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 1→5% MeOH in CH2Cl2 giving the title compound.

Workup

  1. customTHF was evaporated
  2. additionthe mixture was diluted with H2O
  3. extractionextracted with CH2Cl2
  4. dry with materialthe combined organic extracts were dried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with 1→5% MeOH in CH2Cl2 giving the title compound

Sources & evidence

ORD record
ord-6df20a3429794271950b8aba7f77fe58
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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