Dicyclohexylcarbodiimide → Tert-butyl 2,6-dioxomorpholine-4-carboxylate

HRID 417464Notes

Reaction equation

HRID 417464 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10](=[O:12])[O:16][C:14](=[O:15])[CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 2755971N-(tert-Butoxycarbonyl)iminodiacetic Acid

Product 1

HCID 11830836Tert-butyl 2,6-dioxomorpholine-4-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (tert-butoxycarbonyl-carboxymethyl-amino)-acetic acid (5 g, 21.4 mmol) and DCC (4.85 g, 23.6 mmol) in dichloromethane was stirred for 16 hours. The mixture was filtered and the solvent was removed from the filtrate to provide 2,6-dioxo-morpholine-4-carboxylic acid tert-butyl ester (4.86 g, 21.0 mmol, 99%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed from the filtrate

Sources & evidence

ORD record
ord-4c7e920d42894024a3a8363e9dc243ab
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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