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

HRID 79711Notes

Reaction equation

HRID 79711 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-14345934359c40c595f8b7c7f6e48501
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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