Lithium Hydroxide → HCID 86584844, compound

HRID 1006807Notes

Reaction equation

HRID 1006807 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-caaf8898809c4808864f776b4f9c1e76
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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