Piperidine → HCID 131728271, compound

HRID 500299Notes

Reaction equation

HRID 500299 reaction equation
C(N(CC)C(C)C)(C)C.[CH2:10]([N:17]([CH3:28])[C@H:18]([C:20]([C@:22]([CH3:27])([OH:26])[C:23]([OH:25])=O)=[O:21])[CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl>[CH2:10]([N:17]([CH3:28])[C@H:18]([C:20]([C@:22]([CH3:27])([OH:26])[C:23]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:25])=[O:21])[CH3:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 131728272HCID 131728272, compound

Product 1

HCID 131728271HCID 131728271, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5.4 g (41.4 mmol) of N,N-diisopropylethylamine (Hünig's base) and 5.3 g (20.7 mmol) of bis(2-oxo-3-oxazolidinyl)-phosphonium acid chloride (BOP-Cl) are added at 0° C. to a solution of 5.0 g (18.8 mmol) of N-benzyl-N-methyl-L-alanyl-D-lactic acid and 1.6 g (20.7 mmol) of piperidine in 150 ml of methylene chloride, and the mixture is stirred at 0° C. for two hours and then at room temperature for 18 hours. The residual crude product is chromatographed on a silica gel column (silica gel 60—Merck, particle size: 0.04 to 0.063 mm) using the eluent cyclohexane:ethyl acetate (3:1). 3.5 g (55.8% of theory) of N-benzyl-N-methyl-L-alanyl-D-lactic acid piperidide are obtained.

Workup

  1. waitat room temperature for 18 hours
  2. customThe residual crude product is chromatographed on a silica gel column (silica gel 60—Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-012f73c272eb445db94cc24b225c8568
Source dataset
uspto-grants-2010_08
Patent number
US07772190B2

Reaction notes

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