Triethylamine → HCID 21102161, compound

HRID 2355923Notes

Reaction equation

HRID 2355923 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([OH:10])=O)[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[Cl-].[Li+].[CH2:31]([C@@H:38]1[CH2:42][O:41][C:40](=[O:43])[NH:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1.C(Cl)Cl>[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([N:39]2[C@H:38]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:42][O:41][C:40]2=[O:43])=[O:10])[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 433294Lithium ChlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 123189833-(1-Benzothiophen-3-yl)propanoic acid

Product 1

HCID 21102161HCID 21102161, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-benzo[b]thiophen-3-yl-propionic acid (2.1 g, 0.010 mol), triethylamine (4.12 g, 0.040 mol) in anhydrous tetrahydrofuran (100 mL) at 0° C. was added pivaloyl chloride (1.38 mL, 0.011 mol). After stirring for 1.5 h at 0° C., lithium chloride (0.475 g, 0.011 mol) and (R)-4-benzyl-2-oxazolidinone (1.988 g, 0.011 mol) were added. The reaction mixture was allowed to warm up to room temperature and stirred overnight. Then the mixture was washed with water (3×150 mL). The organic layer was separated, dried, and evaporated to give the crude product. The title product was obtained as a brown oil (90%) by flash chromatography on silica gel eluting with 100% methylene chloride. This compound was used immediately in the following procedure.

Workup

  1. temperatureto warm up to room temperature
  2. stirringstirred overnight
  3. washThen the mixture was washed with water (3×150 mL)
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated
  7. customto give the crude product

Sources & evidence

ORD record
ord-b81082d276054b809bc67e63fdcbf517
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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