Triphenylphosphine → 1-(5-tert-Butyl-isoxazol-3-yl)-3-(4-chloro-benzenesulfonyl)-3-methyl-pyrrolidin-2-one

HRID 1924862

Reaction equation

HRID 1924862 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]([C:36]1[O:40][N:39]=[C:38]([NH:41][C:42](=[O:58])[C:43]([S:48]([C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=2)(=[O:50])=[O:49])([CH3:47])[CH2:44][CH2:45]O)[CH:37]=1)([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl>[C:32]([C:36]1[O:40][N:39]=[C:38]([N:41]2[CH2:45][CH2:44][C:43]([S:48]([C:51]3[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=3)(=[O:50])=[O:49])([CH3:47])[C:42]2=[O:58])[CH:37]=1)([CH3:34])([CH3:33])[CH3:35]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58280577N-(5-tert-butyl-isoxazol-3-yl)-2-(4-chlorobenzenesulfonyl)-4-hydroxy-2-methyl-butyramide

Product 1

HCID 446097571-(5-tert-Butyl-isoxazol-3-yl)-3-(4-chloro-benzenesulfonyl)-3-methyl-pyrrolidin-2-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of diethyl azodicarboxylate (0.025 g; 0.14 mmol) in methylene chloride (1 mL) was added triphenylphosphine (0.038 g; 0.14 mmol). The mixture was stirred 20 minutes and N-(5-tert-butyl-isoxazol-3-yl)-2-(4-chlorobenzenesulfonyl)-4-hydroxy-2-methyl-butyramide (0.030 g; 0.072 mmol) in 1 mL methylene chloride was added. After 18 hours the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. Removal of the volatiles from the product-rich fractions provided 0.024 g of product. 1H NMR (CDCl3) δ 7.83 (d, 2H), 7.55 (d, 2H), 6.73 (s, 1H), 4.03 (m, 1H), 3.95 (m, 1H), 3.25 (m, 1H), 2.29 (m, 1H), 1.52 (s, 3H), 1.35 (s, 9H). MS (ESI): m/e 397, 399 (M+H).

Workup

  1. customAfter 18 hours the volatiles were removed in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. customRemoval of the volatiles from the product-rich fractions

Sources & evidence

ORD record
ord-55ff04f36fca42b3853c662356f44264
Source dataset
uspto-grants-2012_05
Patent number
US08178568B2

Linked notes

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