Hydrochloric Acid → HCID 67266314, compound

HRID 1685464Notes

Reaction equation

HRID 1685464 reaction equation
[Li+].[OH-].[F:3][C:4]([F:33])([F:32])[C:5]1[N: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.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]=[N:10][C:5]([C:4]([F:32])([F:33])[F:3])=[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 57539090HCID 57539090, compound

Product 1

HCID 67266314HCID 67266314, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (118 mg, 4.93 mmol) was added to a solution of (2R,4R)-1-tert-butyl 2-methyl 4-(3-(6-(trifluoromethyl)pyridin-3-yl)ureido)piperidine-1,2-dicarboxylate (550 mg, 1.23 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 the 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 500 mg (94%). LC-MS: 433.2, 431.3; (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-e5b878b103d94732a8f40c3111ed62fa
Source dataset
uspto-grants-2012_04
Patent number
US08148401B2

Reaction notes

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