Triphenylphosphine → Thiocholesterol

HRID 1893023Notes

Reaction equation

HRID 1893023 reaction equation
OC1CN[C@H](CO)C1.[CH3:9][CH:10]([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]1[C@:35]2([CH3:36])[C@H:20]([C@H:21]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:24]([CH2:25][C@H:26]([CH2:28][CH2:29]2)[SH:27])=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)[CH3:16])[CH3:11].C([O-])(=O)CCC([O-])=O.[N+](C1C=CC(SSC2C=CC([N+]([O-])=O)=CN=2)=NC=1)([O-])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC(Cl)C.CN(C1C=CN=CC=1)C.C(#N)C.ClC(Cl)C.C(#N)C>[CH3:11][CH:10]([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]1[C@:35]2([CH3:36])[C@H:20]([C@H:21]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:24]([CH2:25][C@H:26]([CH2:28][CH2:29]2)[SH:27])=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)[CH3:16])[CH3:9]

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 164742,2'-Dithiobis(5-nitropyridine)HCID 865981504-Hydroxy-L-prolinol thiocholesterol succinate

Product 1

HCID 65075Thiocholesterol

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 63651,1-DichloroethaneSolventHCID 21218066Acetonitrile dichloroethaneSolvent

Procedure

Succinate 27 (2.1 g, 1.9 mmol) was dissolved in dichloroethane (8 mL). To that solution DMAP (0.228 g, 1.9 mmol) was added. 2,2′-Dithio-bis(5-nitropyridine) (0.58 g, 1.9 mmol) in acetonitrile/dichloroethane (3:1, 8 mL) was added successively. To the resulting solution triphenylphosphine (0.49 g, 1.9 mmol) in acetonitrile (4 ml) was added. The reaction mixture turned bright orange in color. The solution was agitated briefly using wrist-action shaker (5 mins). Long chain alkyl amine-CPG (LCAA-CPG) (12 g, 1860 μmoles, 155 μn/g) was added. The suspension was agitated for 4 h. The CPG was filtered through a sintered funnel and washed with acetonitrile, dichloromethane and ether successively. Unreacted amino groups were masked using acetic anhydride/pyridine. The loading capacity of the CPG 28 was measured by taking UV measurement. (57 μM/g).

Workup

  1. customwrist-action shaker (5 mins)
  2. stirringThe suspension was agitated for 4 h
  3. filtrationThe CPG was filtered through a sintered funnel
  4. washwashed with acetonitrile, dichloromethane and ether successively

Sources & evidence

ORD record
ord-319f4cef314d4b77af9f73005a516bd6
Source dataset
uspto-grants-2013_08
Patent number
US08507661B2

Reaction notes

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