Triphenylphosphine → HCID 11233520, compound

HRID 495130Notes

Reaction equation

HRID 495130 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([O:38][C:39](=[O:45])[NH:40][CH2:41][CH2:42][CH2:43][OH:44])([CH3:37])([CH3:36])[CH3:35].[Cl:46][C:47]1[CH:56]=[CH:55][CH:54]=[C:53]2[C:48]=1[C:49](O)=[CH:50][C:51](=[O:57])[O:52]2>C1COCC1>[C:34]([O:38][C:39](=[O:45])[NH:40][CH2:41][CH2:42][CH2:43][O:44][C:49]1[C:48]2[C:47]([Cl:46])=[CH:56][CH:55]=[CH:54][C:53]=2[O:52][C:51](=[O:57])[CH:50]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateHCID 5363146Diisopropyl azodicarboxylateHCID 546894395-Chloro-4-hydroxy-2H-1-benzopyran-2-one

Product 1

HCID 11233520HCID 11233520, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triphenylphosphine (0.438 g, 1.67 mmol) in 10 mL of THF is cooled to −78° C. and DIAD (0.430 g) is added in one portion. (3-Hydroxy-propyl)-carbamic acid tert-butyl ester (560 mg, 1.3 eq) in 1 mL of THF is added and the solution is allowed to warm to room temperature over the course of 1 hr. The yellow solution is treated with 5-chloro-4-hydroxycoumarin (0.300 g, 1.5 mmol) and is stirred at ambient temperature for 3.5 hrs. The solvent is removed under reduced pressure and the crude product is purified using an ISCO 4 g SiO2 column eluting with ether/heptane gradient to afford the title compound (0.106 g, 20%). 1H NMR (CDCl3, 300 MHz) δ 7.27 (3H, m), 5.71 (1H, s), 4.73 (1H, brs), 4.17 (2H, t, J=5.75 Hz), 3.41 (2H, q, J=6.5 Hz), 2.13 (2H, m), 1.43 (9H, s); MS (ESI, Pos.) calcd for C17H20ClNO5 m/z [M+H+Na]=376.1, found 376.1.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe crude product is purified
  3. washeluting with ether/heptane gradient

Sources & evidence

ORD record
ord-4bec690b98cf4dd19d1c953f95cb4315
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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