Phosgene → HCID 68541954, compound

HRID 1994293Notes

Reaction equation

HRID 1994293 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][CH2:17][NH:18][CH:19]([CH:25]([CH3:27])[CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:37](Cl)(Cl)=[O:38]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:16][CH2:17][N:18]([CH:19]([CH:25]([CH3:26])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:37]2=[O:38])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 68539455HCID 68539455, compound

Product 1

HCID 68541954HCID 68541954, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(2-(4-benzyloxyphenylamino)ethylamino)-3-methylbutyrate (100 mg; 0.27 mmol) was dissolved in toluene (5 ml) and cooled to 0° C. DIEA (141 μl; 0.81 mmol) and phosgene (20% strength in toluene; 202 μl; 0.40 mmol) were added thereto. The mixture was allowed to reach RT over the course of 3 h, and then the solvent was removed under reduced pressure. The residue was partitioned between water (10 ml) and EtOAc (10 ml). The phases were separated and the aqueous phase was extracted with EtOAc (2×; 5 ml). The combined organic phases were dried over MgSO4. After removal of the solvent whilst under reduced pressure, ethyl 2-(3-(4-benzyloxyphenyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (90 mg; 0.22 mmol) was obtained. MS: 397.15 (M+H); Rt: 1.90 min (method: gradient 0 min 90% H2O (0.05% TFA) 1.9 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 10% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

  1. customto reach RT over the course of 3 h
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between water (10 ml) and EtOAc (10 ml)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with EtOAc (2×; 5 ml)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. customAfter removal of the solvent whilst under reduced pressure

Sources & evidence

ORD record
ord-20b202c0c89f40cb86db01cf081054cb
Source dataset
uspto-grants-2010_01
Patent number
US07652143B2

Reaction notes

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