Trityl chloride → HCID 69212763, compound

HRID 902909Notes

Reaction equation

HRID 902909 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][CH:8]([CH2:12][SH:13])[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:15]1([C:21](Cl)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:1]([O:5][C:6](=[O:14])[CH2:7][CH:8]([CH2:12][S:13][C:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:9]([OH:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 87735051HCID 87735051, compound

Product 1

HCID 69212763HCID 69212763, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of the compound of example 25 (8.10 g; 36.77 mmoles) in dry THF (25 mL) at room temperature, was transferred dropwise a solution of triphenylmethyl chloride (12.30 g; 44.13 mmoles) in dry THF (25 mL). The mixture was stirred at room temperature for 24 hours. The solvent was then evaporated under vacuum and the residue was directly subjected to flash chromatography (SiO2, gradient of 15% ethyl acetate in hexanes to 50% ethyl acetate in hexanes) to give 3.50 g (20.6% yield) of the pure desired protected compound: 1H NMR (CDCl3, 400 MHz) 7.50 (d, 6H), 7.29 (m, 9H), 2.58 (m, 5H), 1.45 (S, 9H); 13C NMR (CDCl3, 100 MHz) □179.31, 170.32, 144.34, 129.47, 127.93, 127.81, 126.75, 81.03, 66.93, 40.73, 36.13, 32.66, 27.90.

Workup

  1. customat room temperature
  2. customThe solvent was then evaporated under vacuum
  3. customto give 3.50 g (20.6% yield) of the

Sources & evidence

ORD record
ord-458f781043c843cdb1df3a7672037def
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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