Hydrochloric Acid → (2R,4R)-1-(tert-butoxycarbonyl)-4-(3-(4-cyanophenyl)ureido)piperidine-2-carboxylic Acid

HRID 1971307Notes

Reaction equation

HRID 1971307 reaction equation
[Li+].[OH-].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:31])[NH:13][C@@H:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:16]([C:27]([O:29]C)=[O:28])[CH2:15]2)=[CH:7][CH:6]=1)#[N:4].Cl>C1COCC1.CO.O>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][C@@H:14]([NH:13][C:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:3]#[N:4])=[CH:6][CH:7]=2)=[O:31])[CH2:15][C@@H:16]1[C:27]([OH:29])=[O:28])=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57539094(2R,4R)-1-tert-butyl 2-methyl 4-(3-(4-cyanophenyl)ureido)piperidine-1,2-dicarboxylate

Product 1

HCID 57539001(2R,4R)-1-(tert-butoxycarbonyl)-4-(3-(4-cyanophenyl)ureido)piperidine-2-carboxylic AcidYield 99.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (143 mg, 5.96 mmol) was added to a solution of (2R,4R)-1-tert-butyl 2-methyl 4-(3-(4-cyanophenyl)ureido)piperidine-1,2-dicarboxylate (1200 mg, 2.98 mmol) in THF/MeOH/water (3:2:1) (24 mL) and the resulting solution was stirred at room temperature for 18 hours. 1M HCl solution was added to reaction solution to adjust pH to about 3, extracted with ethyl acetate (2×50 mL). The organic layers were dried over MgSO4 and concentrated to give the acid as a white solid 1150 mg (99%). LC-MS: 389.2, 387.3 (t=2.1 min).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1298859964484bb0aa20553d95f4a34a
Source dataset
uspto-grants-2013_04
Patent number
US08431597B2

Reaction notes

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