4-Oxo-pyrrolidine-1,3-dicarboxylic acid diethyl ester → HCID 178473309, compound

HRID 659046Notes

Reaction equation

HRID 659046 reaction equation
O=[C:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH:3]1[C:12]([O:14]CC)=O.C(=O)(O)O.[NH2:21][C:22]([NH2:24])=[NH:23]>C(O)(C)(C)C>[NH2:24][C:22]1[N:21]=[C:12]([OH:14])[C:3]2[CH2:4][N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][C:2]=2[N:23]=1

Participants

4

Reactant 2

HCID 2763144-Oxo-pyrrolidine-1,3-dicarboxylic acid diethyl esterHCID 286947Carbonic acid-guanidine (1:1)

Product 1

HCID 178473309HCID 178473309, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A suspension of intermediate (f) (14.05 g) and guanidine carbonate (g) (16.6 g, 91.9 mmol) was refluxed in t-butanol (147 mL) for about 6 h. The mixture was allowed to cool to ambient temperature for about 2 h. The volatile components were removed under vacuum and water was added. The pH was adjusted to about 6-7 using KHSO4. The resulting slurry was filtered to collect the solids which were washed with water followed by EtOAc. The solids were dried under vacuum to afford intermediate (h) as cream solids (11.9 g, 53.1 mmol) in 87% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 11.01 (s, 1H), 6.97 (s, 0.5H, possible tautomer), 6.70 (s, 2H), 4.25 (s, 4H), 4.13-4.03 (m, 2H), 1.22 (t, 3H). LCMS (M+H)+: 225.2.

Workup

  1. customThe volatile components were removed under vacuum and water
  2. additionwas added
  3. filtrationThe resulting slurry was filtered
  4. customto collect the solids which
  5. washwere washed with water
  6. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-f0b06a73864d4f16b56147d4a0f050d7
Source dataset
uspto-grants-2011_12
Patent number
US08080556B2

Reaction notes

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