N-(9-Fluorenylmethoxycarbonyloxy)succinimide → 3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2-dimethylpropanoic acid

HRID 74779

Reaction equation

HRID 74779 reaction equation
Cl.[NH2:2][CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([OH:7])=[O:6].[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25](ON3C(=O)CCC3=O)=[O:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1>C([O-])([O-])=O.[Na+].[Na+].COCCOC>[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25]([NH:2][CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([OH:7])=[O:6])=[O:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 534077243-Amino-2,2-dimethylpropanoic acid hydrochloride

Product 1

HCID 450244313-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2-dimethylpropanoic acidYield 99.7%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 3-amino-2,2-dimethylpropanoic acid hydrochloride (1.0 g, 6.5 mmol, 1.0 eq.) in 10 mL of 10% Na2CO3 was added to a solution of 1-{[(9H-fluoren-9-ylmethoxy)carbonyl]oxy}pyrrolidine-2,5-dione (2.3 g, 6.5 mmol, 1.0 eq.) in 10 mL of DME. The reaction was allowed to stir at room temperature overnight. Reaction was concentrated to a smaller volume and then washed two times with ether. The aqueous layer was acidified to pH<2 with concentrated HCl and then extracted three times with a 10% methanol 90% dichloromethane solution. The organics where combined before being washed with 1M HCl and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo producing #124 (2.2 g, 98%) as a white solid. LC-MS (Protocol Q1): m/z 362.0 [M+Na+] retention time=0.89 minutes.

Workup

  1. customReaction
  2. concentrationwas concentrated to a smaller volume
  3. washwashed two times with ether
  4. extractionextracted three times with a 10% methanol 90% dichloromethane solution
  5. washbefore being washed with 1M HCl and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-278e8d3542b44196a5b3f59e1bada9f9
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Linked notes

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