(Phenylthio)acetic acid → HCID 22730197, compound

HRID 2356018Notes

Reaction equation

HRID 2356018 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-f776c4015292410fb9fd5248d00342d0
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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