(Phenylthio)acetic acid → HCID 22730197, compound

HRID 1785763Notes

Reaction equation

HRID 1785763 reaction equation
[C:1]1([S:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[C:18]12([CH2:28][NH2:29])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2.C(N(CC)C(C)C)(C)C>ClCCl.CN(C=O)C>[C:18]12([CH2:28][NH:29][C:9](=[O:11])[CH2:8][S:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:25][CH:24]3[CH2:23][CH:22]([CH2:21][CH:20]([CH2:26]3)[CH2:19]1)[CH2:27]2

Participants

7

Reactant 4

HCID 59541(Phenylthio)acetic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamine

Product 1

HCID 22730197HCID 22730197, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A room temperature solution of (phenylsulfanyl)acetic acid (1.68 g, 10.0 mmol) in dichloromethane (10 mL) was treated with 2M oxalyl chloride in dichloromethane (8 mL, 16.0 mmol) and DMF (1 drop), stirred for 2 hours, concentrated, dissolved in dichloromethane (10 mL), treated with 1-adamantylmethylamine (1.65 g, 10.0 mmol) and N,N-diisopropylethylamine (2.1 mL, 12.0 mmol), and stirred for 1 hour. The mixture was filtered through a pad of silica gel (20 g) and concentrated to provide the desired product of sufficient purity for subsequent use.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in dichloromethane (10 mL)
  3. stirringstirred for 1 hour
  4. filtrationThe mixture was filtered through a pad of silica gel (20 g)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7039c37502a1457bad3ef806fc527a82
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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