Trityl chloride → 3-[(Triphenylmethyl)sulfanyl]propanoic acid

HRID 444608Notes

Reaction equation

HRID 444608 reaction equation
[CH2:1]([C:4]([OH:6])=[O:5])[CH2:2][SH:3].[C:7]1([C:13](Cl)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[C:13]([S:3][CH2:2][CH2:1][C:4]([OH:6])=[O:5])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 65143-Mercaptopropionic Acid

Product 1

HCID 2627673-[(Triphenylmethyl)sulfanyl]propanoic acidYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mercaptopropionic acid 2 (3.14 g) was dissolved in 50 ml of methylene chloride. Triphenylmethylchloride 3 (8.36 g, 30 mmol) was added to that, and 19-hour protection reactions were carried out at room temperature. The precipitate generated through the protection reactions was filtered and gathered, and was rinsed with 40 ml of diethyl ether. The precipitate was then dried under reduced pressure, to form 9.86 g of 3-(tritylthio)propanoic acid 4, which is a white solid.

Workup

  1. customwere carried out at room temperature
  2. filtrationwas filtered
  3. washwas rinsed with 40 ml of diethyl ether
  4. customThe precipitate was then dried under reduced pressure

Sources & evidence

ORD record
ord-d22b357b1eb6472fa57171c45f1cc5ab
Source dataset
uspto-grants-2013_07
Patent number
US08475685B2

Reaction notes

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