N,N-Dimethylglycine → HCID 15293153, compound

HRID 129061Notes

Reaction equation

HRID 129061 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:6]2=[N:5][C:4]([O:12][CH2:13][N:14]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][C:20]([O:29][CH2:30][CH2:31][OH:32])=[CH:21][C:22]=3[CH:26]([CH3:28])[CH3:27])[S:15]2(=[O:17])=[O:16])=[CH:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:48][N:49]([CH3:54])[CH2:50][C:51](O)=[O:52]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:6]2=[N:5][C:4]([O:12][CH2:13][N:14]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][C:20]([O:29][CH2:30][CH2:31][O:32][C:51]([CH2:50][N:49]([CH3:54])[CH3:48])=[O:52])=[CH:21][C:22]=3[CH:26]([CH3:27])[CH3:28])[S:15]2(=[O:17])=[O:16])=[CH:3]1

Participants

6

Reactant 3

HCID 673N,N-DimethylglycineHCID 10868DicyclohexylcarbodiimideHCID 15293152HCID 15293152, compound

Product 1

HCID 15293153HCID 15293153, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 12 (0.8 g, 1.72 mmol) in CH2Cl2 (25 mL) containing 1,3-dicyclohexylcarbodiimide (1.06 g, 5.14 mmol) was added dimethyl glycine (0.19 g, 1.9 mmol), followed by 4-dimethylaminopyridine (0.21 g, 1.72 mmol). The mixture was stirred at room temperature for 2 hours, the solvent was removed in vacuo, and the residue was purified by column chromatography on silica eluting with 10% methanol/ethyl acetate to afford 0.64 g (68%) of 2-[4-oxo-6,7,8,9-tetrahydro-4H-pyrido-[1,2-a]pyrimidin-2-yl]oxymethyl-4-isopropyl-6-[2-(dimethylaminomethylcarbonyloxy)ethoxy]saccharin as a white foam.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography on silica eluting with 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-278d13e0eb894f9389aadff89b4cafa1
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Reaction notes

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