Tetrahydrofuran → HCID 53771767, compound

HRID 611598Notes

Reaction equation

HRID 611598 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1N=C(OC)N=C(OC)N=1.C1COCC1.Cl.[CH2:34]([O:36][C:37](=[O:41])[CH2:38][CH2:39][NH2:40])[CH3:35]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=[O:16])[NH:40][CH2:39][CH2:38][C:37]([O:36][CH2:34][CH3:35])=[O:41])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 53771767HCID 53771767, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4.59 g of (RS)-piperidine-1,3-dicarboxylic acid 1-tert.-butyl ester, 3.51 g of 2-chloro4,6-dimethoxy-[1,3,5]-triazine (CDMT), 60 ml of THF and 2.25 ml of N-MM are stirred under argon at 0° C. for 3 hrs. After the addition of 3.07 g of β-alanine ethyl ester hydrochloride and 2.25 ml of N-MM the mixture is stirred at RT for 18 hrs. The reaction mixture is diluted with ethyl acetate and washed in sequence with ice-cold dilute hydrochloric acid, water, dilute sodium carbonate solution, water and saturated sodium chloride solution. After drying over sodium sulphate and evaporation of the solvent there are obtained 6.16 g of (RS)-3-(2-ethoxycarbonyl-ethylcarbamoyl)-piperidine-1-carboxylic acid tert.-butyl ester as a pale yellow oil. MS: 329 (M+H)+.

Workup

  1. washwashed in sequence with ice-cold dilute hydrochloric acid, water, dilute sodium carbonate solution, water and saturated sodium chloride solution
  2. dry with materialAfter drying over sodium sulphate and evaporation of the solvent there

Sources & evidence

ORD record
ord-f05e365207ce4b0e9cadb6b65e45f4c5
Source dataset
uspto-grants-1999_12
Patent number
US06001855

Reaction notes

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