Lithium hydroxide, monohydrate → HCID 86756071, compound

HRID 1859358Notes

Reaction equation

HRID 1859358 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:38])[CH2:13][CH2:14][N:15]([CH:27]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[C:28](=[O:31])[NH:29][OH:30])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+]>C(O)C.O>[OH2:3].[CH:32]1([CH:27]([N:15]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:14][CH2:13][C:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[O:38])[C:28](=[O:31])[NH:29][OH:30])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86756073HCID 86756073, compound

Product 1

HCID 86756071HCID 86756071, compoundYield 164.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 1-{3-[(cyclohexylhydroxycarbamoylmethyl)(4-methoxybenzenesulfonyl) amino]propionyl}piperidine-4-carboxylic acid ethyl ester (0.62 grams, 1.16 mmol) (Example 17) in ethanol (45 mL) and water (5 mL) was added lithium hydroxide monohydrate (0.24 grams, 5.72 mmol). After stirring for 3 hours at room temperature ethanol-washed Amberlite IR-120 plus ion exchange resin (6 grams) was added. Stirring was continued for 15 minutes and then the mixture was filtered. The filtrate was concentrated in vacuo to give 1-{3-[(cyclohexylhydroxycarbamoylmethyl)-(4-methoxy-benzenesulfonyl)amino]propionyl}-piperidine-4-carboxylic acid monohydrate as a white solid (0.52 grams, 88%). MS: 526 (M+1). Analysis calculated for C24H35N3O8S·H2O: C, 53.05; H, 6.86; N, 7.73. Found: C, 53.53; H, 7.15; N, 7.70.

Workup

  1. washwashed Amberlite IR-120 plus ion exchange resin (6 grams)
  2. additionwas added
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1aedb44ac16b46b0b46d31d176a5f98e
Source dataset
uspto-grants-2000_11
Patent number
US06153609

Reaction notes

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