1-Adamantanecarbonyl chloride → HCID 24955695, compound

HRID 448032Notes

Reaction equation

HRID 448032 reaction equation
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[CH3:12])[CH2:3][CH2:4][CH3:5].[C:13]12([C:23](Cl)=[O:24])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2>C(Cl)Cl.CN(C1C=CN=CC=1)C.CS(C)=O.CO>[C:13]12([C:23](=[O:24])/[CH:12]=[C:7]3\[S:8][CH:9]=[C:10]([CH3:11])[N:6]\3[CH2:2][CH2:3][CH2:4][CH3:5])[CH2:20][CH:19]3[CH2:18][CH:17]([CH2:16][CH:15]([CH2:21]3)[CH2:14]1)[CH2:22]2

Participants

6

Reactant 2

HCID 989151-Adamantanecarbonyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

Product 1

HCID 24955695HCID 24955695, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

In a 20 mL vial a solution of 3-butyl-2,4-dimethylthiazol-3-ium iodide (47.92 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL) was added, followed by the addition of DMAP (49.24 mg, 0.40 mmol) dissolved in CH2Cl2 (0.8 mL). Then, to the solution was added 1-adamantyl carbonylchloride (31.8 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL). The vial was capped and shaken overnight at room temperature. The residue was dissolved in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR, MS and LC/MS. MS (ESI) positive ion 332 (M+H).

Workup

  1. additionwas added
  2. customThe vial was capped
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-b2b399326ca24a5d87523d292f1f048c
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

Loading…