HCID 57654652, compound → HCID 59558468, compound

HRID 1175166Notes

Reaction equation

HRID 1175166 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1([C:12](=[C:14]2C(=O)OC(C)(C)[O:16][C:15]2=O)[OH:13])[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:7]1[C:15](=[O:16])[CH:14]=[C:12]([OH:13])[C:8]21[CH2:11][CH2:10][CH2:9]2)=[O:24])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 57654652HCID 57654652, compound

Product 1

HCID 59558468HCID 59558468, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

{1-[(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-hydroxy-methyl]-cyclobutyl}-carbamic acid tert-butyl ester (1.2 g, 3.5 mmol) is refluxed in ethyl acetate for 4 hours. The solvent is removed in vacuo and the resulting residue is crystallized from ether. 1H-NMR (400 MHz; DMSO-d6): 12.5 (s, 1H), 4.73 (s, 1H), 2.87 (dt, 2H), 2.35-2.25 (m, 2H), 1.85 (quint, 2H), 1.51 (s, 9H); LC-MS (m/z, ES−): 238 (M−H), Retention time: 2.24 mins (LC-MS method 3)

Workup

  1. customThe solvent is removed in vacuo
  2. customthe resulting residue is crystallized from ether

Sources & evidence

ORD record
ord-6d8c9afa29f5404fa815a12f2529f707
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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