Lithium hydroxide, monohydrate → 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoic acid

HRID 1428799Notes

Reaction equation

HRID 1428799 reaction equation
O.[OH-].[Li+].[C:4]([O:8][C:9]([NH:11][S:12]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH3:29])[C:24]([O:26]CC)=[O:25])=[CH:19][CH:18]=1)(=[O:14])=[O:13])=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.O1CCCC1>[C:4]([O:8][C:9]([NH:11][S:12]([NH:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]([CH3:29])[C:24]([OH:26])=[O:25])=[CH:21][CH:22]=1)(=[O:14])=[O:13])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86680233ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoate

Product 1

HCID 866802342-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoic acidYield 65.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (826 mg, 19.68 mmol) in water (10 mL) was added to a solution of ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoate (3.8 g, 9.84 mmol) in tetrahydrofuran (30 mL) at 0° C. and stirred at room temperature for 18 h. The volatiles were evaporated; the residue diluted with water (50 mL) and extracted with diethyl ether (2×20 mL). The aqueous layer was acidified (pH ˜5) with acetic acid at 0° C., precipitated solid was filtered and dried under reduced pressure to afford 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoic acid (2.3 g, 56%) as white solid.

Workup

  1. customThe volatiles were evaporated
  2. additionthe residue diluted with water (50 mL)
  3. extractionextracted with diethyl ether (2×20 mL)
  4. customat 0° C.
  5. customprecipitated solid
  6. filtrationwas filtered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-e7cc8eb07c66413abfcef8283eb139d6
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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