Triethylamine → HCID 86723491, compound

HRID 2201254Notes

Reaction equation

HRID 2201254 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C@@H:8]1[CH2:16][CH2:15][CH:14]([C:17]2[O:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[C:13]2[N:9]1[C:10]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[C:11]1[C:26](=[O:27])[N:25]([CH3:28])[C:24](=[O:29])[N:23]([CH3:30])[C:12]1=2.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][C@@H:8]1[CH2:16][CH2:15][CH:14]([C:17]2[O:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[C:13]2[N:9]1[C:10]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[C:11]1[C:26](=[O:27])[N:25]([CH3:28])[C:24](=[O:29])[N:23]([CH3:30])[C:12]1=2)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86723492HCID 86723492, compound

Product 1

HCID 86723491HCID 86723491, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.483 mL, 6.20 mmol) was added to a solution of (7S)-7-(hydroxyl methyl)-1,3-dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (1.3 g, 3.10 mmol) and triethylamine (1.296 mL, 9.30 mmol) in DCM (30 mL). The mixture was stirred at room temp. for 105 mins. The reaction was quenched with saturated NaHCO3(aq) and extracted with DCM. The organic extract was passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 40-75% EtOAc/hexane, afforded the title compound.

Workup

  1. customThe reaction was quenched with saturated NaHCO3(aq)
  2. extractionextracted with DCM
  3. extractionThe organic extract
  4. customevaporated under vacuum
  5. customPurification by chromatography on silica
  6. washeluting with 40-75% EtOAc/hexane

Sources & evidence

ORD record
ord-2127d5e1155042e28e85bec9eed338fd
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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