L-Lactic Acid → HCID 68759916, compound

HRID 1945837Notes

Reaction equation

HRID 1945837 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:14](O)(=[O:18])[C@H:15]([CH3:17])[OH:16].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[OH:16][CH:15]([CH3:17])[C:14]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)=[O:18]

Participants

5

Reactant 3

HCID 107689L-Lactic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68759916HCID 68759916, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl piperazine-1-carboxylate (0.367 g), L-(+)-lactic acid (0.213 g), and HBTU (0.822 g) was stirred at rt overnight. Diluted with DCM, the mixture was washed with water (2×), brine, and dried (Na2SO4). Filtration and concentration gave 1-tert-butyl 4-(2-hydroxypropanoyl)piperazine-1-carboxylate as viscous oil, which was treated with trifluoroacetic acid in dichloromethane. After concentration, the residue was reacted with 4-(8-(bromomethyl)-9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-9H-purin-6-yl)morpholine in the presence of diisopropylethylamine (10 eq) following General Procedure E of amine alkylation to give 269. LCMS: M+H+=520.3

Workup

  1. washthe mixture was washed with water (2×), brine
  2. dry with materialdried (Na2SO4)
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-a5d10269737e43a9859ff9098165f156
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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