Hydrochloric Acid → HCID 69652395, compound

HRID 2212186Notes

Reaction equation

HRID 2212186 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH:10]([C:12]([O:14]CC)=[O:13])[CH2:9][N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:7]1)=[O:5])[CH3:2].Cl>P([O-])([O-])([O-])=O.O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9][N:8]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69652397HCID 69652397, compound

Product 1

HCID 69652395HCID 69652395, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1061PhosphateSolvent

Procedure

Add lipase (1.7 g, Amano AY30) to a slurry of piperidine-1,3,5-tricarboxylic acid 1-tert-butyl ester 3,5-diethyl ester (5.8 g, 17.6 mmol) in pH 7.2 phosphate buffer (58 mL). Stir 48 H, dilute with water then acidify to pH 2.5 with 1N HCl. Extract 3× with EtOAc. Wash with brine, dried over Na2SO4, filter and concentrate to dryness to give the title compound (5.0 g, 94%) as a mixture of cis isomers as a white solid. MS(IS) 300.2 (M−1); Anal. Calc'd for C14H23NO6.0.5CHCl3: C, 54.91; H, 7.56; N, 4.56. Found: C, 54.90; H, 7.59; N, 4.55.

Workup

  1. extractionExtract 3× with EtOAc
  2. washWash with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-f3887400efe748e994938734b2885761
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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