Lithium Hydroxide → HCID 86584844, compound

HRID 458336Notes

Reaction equation

HRID 458336 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:32]=[CH:31][C:7]([C:8]([NH:10][CH2:11][C@@H:12]2[CH2:16][C@@H:15]([SH:17])[CH2:14][N:13]2[S:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)(=[O:20])=[O:19])=[O:9])=[CH:6][CH:5]=1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C1COCC1>[SH:17][C@H:15]1[CH2:14][N:13]([S:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)(=[O:19])=[O:20])[C@H:12]([CH2:11][NH:10][C:8](=[O:9])[C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:33])=[O:2])=[CH:32][CH:31]=2)[CH2:16]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 86584845HCID 86584845, compound

Product 1

HCID 86584844HCID 86584844, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A degassed solution of 102 mg (0.21 mmol) (2S,4R)-N-[4-mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-ylmethyl]-terephthalamic acid methyl ester in 12.6 ml THF was treated with 12.6 ml 0.1 M aqueous LiOH (1.26 mmol, 6 eq) at 0° C. and was stirred at room temperature for 1.5 h. 1 M KHSO4 solution was added (pH 2), the layers were separated and the inorganic one was extracted with EtOAc. The combined organic ones were washed with water and brine, dried over Na2SO4 and evaporated, yielding (2S,4R)-N-[4-mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-ylmethyl]-terephthalamic acid as white foam, MS: 471 (MH+).

Workup

  1. customthe layers were separated
  2. extractionthe inorganic one was extracted with EtOAc
  3. washThe combined organic ones were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-263f545f82dd49998d2a9951f8d87d4e
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

Loading…