Lithium Hydroxide → HCID 86649837, compound

HRID 2098258Notes

Reaction equation

HRID 2098258 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][NH:6][C:7]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:17])=[O:8])C.[OH-].[Li+]>O1CCCC1>[C:28]([O:27][C:25]([NH:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][C:16]([NH:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][C:7]([NH:6][CH2:5][C:4]([OH:32])=[O:3])=[O:8])=[O:17])=[O:26])([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86649838HCID 86649838, compound2×

Product 1

HCID 86649837HCID 86649837, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-{2-[2-(2-t-Butoxycarbonylaminoethoxy)ethoxycarbonylamino]ethoxy}ethoxycarbonylamino)acetic acid ethyl ester (Compound 5, 12.2 g, 0.026 mol) was dissolved in tetrahydrofuran (THF, 150 mL) and then stirred. After slowly adding 2 N lithium hydroxide (LiOH) aqueous solution (40 mL), the mixture was stirred at room temperature for 40 minutes. After removing THF from the reaction mixture, 1 N HCl was slowly added for acidification. After extracting 3 times with dichloromethane, the organic layer was separated, dried with magnesium sulfate, and then concentrated. The target compound (2-{2-[2-(2-t-butoxycarbonylaminoethoxy)ethoxycarbonylamino]ethoxy}ethoxycarbonylamino)acetic acid (Compound 7, 11 g, 90.1%) was yielded.

Workup

  1. stirringthe mixture was stirred at room temperature for 40 minutes
  2. customAfter removing THF from the reaction mixture, 1 N HCl
  3. additionwas slowly added for acidification
  4. extractionAfter extracting 3 times with dichloromethane
  5. customthe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bcb4a5e0d010410b92880223f33273d1
Source dataset
uspto-grants-2013_05
Patent number
US08450469B2

Reaction notes

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