Hydrochloric Acid → 6-((1-(((3,5-Dichlorobenzyl)oxy)carbonyl)piperidin-4-yl)amino)-6-oxohexanoic acid

HRID 1480379Notes

Reaction equation

HRID 1480379 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)=[O:19])[CH2:14][CH2:13]1)=[O:10])C.O[Li].O.Cl>C1COCC1.O.CCOC(C)=O>[Cl:28][C:26]1[CH:27]=[C:22]([CH:23]=[C:24]([Cl:29])[CH:25]=1)[CH2:21][O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:9](=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:30])=[O:3])[CH2:13][CH2:14]1)=[O:19]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 867226333,5-Dichlorobenzyl 4-(6-ethoxy-6-oxohexanamido)piperidine-1-carboxylate

Product 1

HCID 867226326-((1-(((3,5-Dichlorobenzyl)oxy)carbonyl)piperidin-4-yl)amino)-6-oxohexanoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3,5-dichlorobenzyl 4-(6-ethoxy-6-oxohexanamido)piperidine-1-carboxylate (step 1) (130 mg, 0.283 mmol) in THF (3 mL)/water (1 mL) was added LiOH.H2O (26.1 mg, 0.623 mmol) and the reaction mixture stirred at RT for 3 hrs. The resulting mixture was diluted with water and EtOAc and the aqueous portion acidified with 0.1 M HCl solution (pH 5-6). The resulting precipitate was collected by filtration and washed with water to afford the title product;

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-027b68c76d3349f5860a911c93bb1cfd
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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