Diisopropyl azodicarboxylate → (5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[(5-Ethyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-one

HRID 1452594Notes

Reaction equation

HRID 1452594 reaction equation
[CH2:1]([C:3]1[NH:7][N:6]=[N:5][N:4]=1)[CH3:2].N([CH2:11][C@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[C:22]([F:24])[C:21]([C:25]3[CH2:26][CH2:27][S:28](=[O:32])(=[O:31])[CH2:29][CH:30]=3)=[C:20]([F:33])[CH:19]=2)[CH2:13]1)=[N+]=[N-].CC(OC(/N=N/C(OC(C)C)=O)=O)C>ClCCl>[O:32]=[S:28]1(=[O:31])[CH2:27][CH:26]=[C:25]([C:21]2[C:22]([F:24])=[CH:23][C:18]([N:14]3[CH2:13][C@H:12]([CH2:11][N:5]4[N:6]=[N:7][C:3]([CH2:1][CH3:2])=[N:4]4)[O:16][C:15]3=[O:17])=[CH:19][C:20]=2[F:33])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 5363146Diisopropyl azodicarboxylateHCID 86598351HCID 86598351, compoundHCID 178438076HCID 178438076, compound

Product 1

HCID 10048818(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[(5-Ethyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-oneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Ethyl-1H-tetrazole (0.164 g, 1.67 mmol), (5R)-3-[4-(1,1-dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-(hydroxymethyl)oxazolidin-2-one (WO 01/81350 A1) (0.30 g, 0.84 mmol), and polystyrene-triphenylphosphine (1.73 mmol/g loading: Argonaut Technologies, Inc. Foster City, Calif. USA, 1.46 g, 2.53 mmol) were dissolved in dry dichloromethane (30 ml). Diisopropylazodicarboxylate (0.33 ml, 1.68 mmol) was added and the mixture was stirred at room temperature for 16 hours. The resin was filtered off and rinsed with dichloromethane. The filtrate was evaporated to dryness and purified by chromatography on silica gel with 10% acetonitrile in dichloromethane. The material obtained after chromatography was precipitated from dichloromethane with diethyl ether to yield the title compound as a white powder (0.26 g, 71%).

Workup

  1. filtrationThe resin was filtered off
  2. washrinsed with dichloromethane
  3. customThe filtrate was evaporated to dryness
  4. custompurified by chromatography on silica gel with 10% acetonitrile in dichloromethane
  5. customThe material obtained after chromatography
  6. customwas precipitated from dichloromethane with diethyl ether

Sources & evidence

ORD record
ord-c4aef61e8e6e42e0b701856ea455e4ab
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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