Triphenylphosphine → HCID 178455456, compound

HRID 1364306Notes

Reaction equation

HRID 1364306 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:17])([CH3:16])[C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14]O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:37]1([N:43]2[C:47]([SH:48])=[N:46][N:45]=[N:44]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([SiH2:5][O:6][C:7]([CH3:17])([CH3:16])[C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][S:48][C:47]2[N:43]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:44]=[N:45][N:46]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178455454HCID 178455454, compoundHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 178455456HCID 178455456, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [trans-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-methanol (prepared as described in J. Med. Chem. (2001), 44, 531, 9.0 g, 34.8 mmol) in THF (100 mL) were added PPh3 (13.7 g, 1.5 eq.), 1-phenyl-1H-tetrazole-5-thiol (6.2 g, 1 eq.) and DIAD (10.3 mL, 1.5 eq.). The reaction mixture was stirred at rt overnight. After evaporation to dryness, the residue was chromatographed over SiO2 (Hex-EA 8-1) to afford the title sulfide (11.4 g) contaminated with some PPh3.

Workup

  1. customAfter evaporation to dryness
  2. customthe residue was chromatographed over SiO2 (Hex-EA 8-1)

Sources & evidence

ORD record
ord-ad05ea30ded04581aaf680f933ee91ce
Source dataset
uspto-grants-2011_02
Patent number
US07888359B2

Reaction notes

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