Acetic Anhydride → HCID 178473801, compound

HRID 46133Notes

Reaction equation

HRID 46133 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH3:22])([CH2:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:12](=[O:14])[N:13]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].C(N(C(C)C)CC)(C)C>C(Cl)Cl.[Cl-].[Na+].O>[C:23]([N:19]1[CH2:20][CH2:21][CH:16]([CH2:15][C:11]2([CH3:22])[S:10][C:9]([NH:8][C@H:2]3[CH2:3][CH:4]4[CH2:7][CH:1]3[CH2:6][CH2:5]4)=[N:13][C:12]2=[O:14])[CH2:17][CH2:18]1)(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 178422083HCID 178422083, compound

Product 1

HCID 178473801HCID 178473801, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-5-(piperidin-4-ylmethyl)thiazol-4(5H)-one (130 mg, 0.41 mmol), acetic anhydride (Aldrich, 83 mg, 0.81 mmol) and diisopropylethylamine (157 mg, 1.22 mmol) in CH2Cl2 (3 mL) was stirred at room temperature for ca. 18 h. Brine was then added, and the mixture was extracted with CH2Cl2 (4×60 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography (silica gel, 0-3.5% MeOH in CH2Cl2) afforded the title compound as a colorless thin film (116 mg). MS (ESI, pos. ion) m/z: 364 (M+H).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (4×60 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c8e3abac13349f3be516704f3e333d7
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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