Lithium Hydroxide → HCID 89459914, compound

HRID 1776507Notes

Reaction equation

HRID 1776507 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:28]=[CH:27][C:16]([CH2:17][N:18]([CH3:26])[CH2:19][C:20]([O:22]CC=C)=[O:21])=[CH:15][CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]([CH3:26])[CH2:19][C:20]([OH:22])=[O:21])=[CH:27][CH:28]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89459916HCID 89459916, compound

Product 1

HCID 89459914HCID 89459914, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl 2-((4-(N-(tert-butoxycarbonyl)methylsulfonamido)-benzyl)(methyl)amino)acetate (0.390 g, 0.945 mmol) in THF (22 ml), LiOH 1N (0.945 ml, 0.945 mmol) was added, and the mixture was stirred at RT for 3 days. The mixture was diluted with water and washed twice with EtOAc. The aqueous phase was acidified with 0.189 ml of HCl 1N and frozen dry. The residue was dissolved in DCM/MeOH and transferred in a small container. 2-((4-(N-(tert-butoxycarbonyl)methylsulfonamido)-benzyl)(methyl)amino)acetic acid was obtained (0.313 g, 0.840 mmol, 89% yield, MS/ESI+ 373.2 [MH]+) and used without any further purification.

Workup

  1. washwashed twice with EtOAc
  2. temperaturefrozen
  3. customdry
  4. dissolutionThe residue was dissolved in DCM/MeOH

Sources & evidence

ORD record
ord-53958589bf14489a9c5b5c9843adcdf7
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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