Trityl chloride → HCID 11509792, compound

HRID 2403080Notes

Reaction equation

HRID 2403080 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.Cl[C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[C:14]1([C:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[S:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 33905114-Mercaptophenylacetic acid

Product 1

HCID 11509792HCID 11509792, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-mercaptophenylacetic acid (369.6 mg, 2.2 mmol) was added to the solution of chlorotriphenylmethane (557.6 mg, 2 mmol) in 2.0 mL of anhydrous dichloromethane. The solution was stirred for 2 hrs under nitrogen. The reaction was quenched by 1N NaOH (3 mL). The suspension was extracted with 10 mL of ethyl acetate, and the organic phase was washed with brine (5 mL×3) and dried over anhydrous magnesium sulfate. The solvent was removed and residue was purified by flash chromatography on silica gel (eluent: ethyl acetate/hexane=⅓) to afford 713.4 mg of desired product (87%). 1H NMR (400 MHz, CDCl3) δ 7.43-7.40 (m, 6H), 7.26-7.17 (m, 9H), 6.93 (m, 4H), 3.52 (s, 2H) ESI-MS: observed [M+Na]+: 433.6, calculated: 410.5.

Workup

  1. customThe reaction was quenched by 1N NaOH (3 mL)
  2. extractionThe suspension was extracted with 10 mL of ethyl acetate
  3. washthe organic phase was washed with brine (5 mL×3)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. customresidue was purified by flash chromatography on silica gel (eluent: ethyl acetate/hexane=⅓)

Sources & evidence

ORD record
ord-587abf1de0e249efa884e1871455e28b
Source dataset
uspto-grants-2014_08
Patent number
US08802387B2

Reaction notes

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