Triphenylphosphine → HCID 70145158, compound

HRID 2306083Notes

Reaction equation

HRID 2306083 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH2:32]([O:39][NH:40][C:41](=[O:54])[CH2:42][C@H:43](O)[CH2:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([Br:52])=[CH:48][CH:47]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1.CN(C=O)C>[CH2:32]([O:39][N:40]1[C@@H:43]([CH2:44][O:45][C:46]2[CH:51]=[CH:50][C:49]([Br:52])=[CH:48][CH:47]=2)[CH2:42][C:41]1=[O:54])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 88173674HCID 88173674, compound

Product 1

HCID 70145158HCID 70145158, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of triphenylphosphine (121 g) in THF (1.9 L) was treated with DEAD (80.1 g) over 30 minutes, treated with a solution of Example 3D in DMF (600 mL) at 40° C. by cannula over 90 minutes and a solution of triphenylphosphine (6.2 g) and DEAD (3.8 mL) in THF (20 mL), concentrated, treated with toluene (350 mL), and concentrated. The concentrate was treated with toluene (1.9 L), washed with water, and concentrated to half of its original volume, to provide a solution of (4R)-1-(benzyloxy)-4-((4-bromophenoxy)-methyl)-2-azetidinone. 1H NMR (300 MHz, CDCl3) δ7.4 (m, 7H), 6.70 (m, 2H), 5.00 (d, 1H, J=10), 4.92 (d, 1H, J=12 Hz), 3.86 (m, 1H), 3.82 (dd, 1H, J=1, 4 Hz), 2.81 (dd, 1H, J=6, 15 Hz), 2.66 (dd, 1H, J=2, 15 Hz).

Workup

  1. concentrationa solution of triphenylphosphine (6.2 g) and DEAD (3.8 mL) in THF (20 mL), concentrated
  2. additiontreated with toluene (350 mL)
  3. concentrationconcentrated
  4. additionThe concentrate was treated with toluene (1.9 L)
  5. washwashed with water
  6. concentrationconcentrated to half of its original volume

Sources & evidence

ORD record
ord-69c1b88895f24745bd440c56a6141997
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Reaction notes

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