Dichloromethane → HCID 18367272, compound

HRID 2379554Notes

Reaction equation

HRID 2379554 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:17]1[C:21](=[O:22])[CH2:20][CH2:19][C@H:18]1[C:23](O)=O.C1CCC([N:32]=C=NC2CCCCC2)CC1.C(Cl)Cl>CN(C1C=CN=CC=1)C.O.C(Cl)(Cl)Cl.CO>[C:11]1([C:9]2[N:32]=[C:23]([CH:18]3[NH:17][C:21](=[O:22])[CH2:20][CH2:19]3)[O:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 7405L-Pyroglutamic AcidHCID 8400BenzoinHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 18367272HCID 18367272, compoundYield 72.3%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of benzoin (45.19 g, 0.21 mol), pyroglutamic acid (25.00 g, 0.19 tool), DCC (47.91 g, 0.23 mol), DMAP (catalytic quantity) and CH2Cl2 (600 mL) was stirred at room temperature. After about 7 hours, the mixture was filtered, concentrated and diluted with AcOH (650 mL). NH4OAc (75.00 g, 0.97 mol) was added and the mixture heated at reflux for about 1.25 hours before being cooled, diluted with H2O and extracted with CH2Cl2. The combined extracts were washed with H2O (3 times), dried over Na2SO4 and concentrated in vacuo to give a yellow solid. Chromatography on a column of silica gel using a mixture of CHCl3 and MeOH (99:1) as eluent afforded 5-(4,5-diphenyl-2-oxazolyl) -2-pyrrolidinone (42.58 g, 72%). An analytical sample was recystallised from CH2Cl2 and hexanes and had mp 145-147° C. IR (KBr)1700 (NH.CO) cm-1 ; 1H NMR (DMSO-d6) δ2.15-2.60 (4H, m, CH2), 4.89 (1H, m, CHN), 7.10-7.70 (10H, m, aromatic H), 8.33 (1H, s, NH); MS m/z 305 (MH+).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. additiondiluted with AcOH (650 mL)
  4. temperaturethe mixture heated
  5. temperatureat reflux for about 1.25 hours
  6. temperaturebefore being cooled
  7. extractionextracted with CH2Cl2
  8. washThe combined extracts were washed with H2O (3 times)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customto give a yellow solid

Sources & evidence

ORD record
ord-3a7bd53d82a04b6b99c80b91abaafac8
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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