4-Nitrobenzenesulfonyl chloride → HCID 70201301, compound

HRID 456251Notes

Reaction equation

HRID 456251 reaction equation
[NH2:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][C@H:3]1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.[N+:29]([C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1)([O-:31])=[O:30]>C(Cl)Cl>[CH2:7]([N:5]1[CH2:6][C@@H:2]([NH:1][S:38]([C:35]2[CH:34]=[CH:33][C:32]([N+:29]([O-:31])=[O:30])=[CH:37][CH:36]=2)(=[O:39])=[O:40])[C@H:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:4]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 68019346HCID 68019346, compound

Product 1

HCID 70201301HCID 70201301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3R,4R)-4-amino-1-benzylpyrrolidin-3-ylcarbamate (5.8 g, 20 mmol) in 100 mL of CH2Cl2, triethylamine (4.04 g, 40 mmol) was added following by addition of 4-nitrobenzenesulfonyl chloride (1.1 eq) and the mixture was stirred at room temperature overnight. The reaction was quenched with saturated aqueous NH4Cl, 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 1-2% MeOH in CHCl3 to give the title product.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with CH2Cl2
  3. dry with materialthe combined organic extracts were dried with Na2SO4
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel eluting with 1-2% MeOH in CHCl3

Sources & evidence

ORD record
ord-9ad065574b49420a92420c08d0bd5f8b
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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