1,1'-Carbonyldiimidazole → HCID 19068519, compound

HRID 1957777Notes

Reaction equation

HRID 1957777 reaction equation
[C:1]([NH:4][CH:5]([CH2:9][C:10]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[NH2:19])=[O:11])[C:6]([OH:8])=O)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:32][C@H:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:34][OH:35]>CN(C=O)C>[C:1]([NH:4][CH:5]([CH2:9][C:10]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[NH2:19])=[O:11])[C:6]([NH:32][CH:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:34][OH:35])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2724025(R)-beta-aminophenethyl alcoholHCID 10755519HCID 10755519, compound

Product 1

HCID 19068519HCID 19068519, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirred solution of 2-acetamido-4-(2-amino-5-chlorophenyl)-4-oxo-butyric acid (0.569 g; 2 mmol) in dry DMF (8 ml), 1,1'-carbonyldiimidazole (0.34 g; 2.1 mmol) was added portionwise at 5°-8° C. under nitrogen. After stirring at 5° C. for 1.5 h, (R)-(-)-2-amino-2-phenylethanol (0.33 g; 2.4 mmol) in dry DMF (6 ml) was added dropwise at 3°-5° C. The reaction was then stirred for 2 h in an ice bath and 16 h at room temperature, quenched with water and extracted with ethyl acetate. The organic layer was washed with water, dried with an. sodium sulfate and concentrated to dryness. The residue was purified by flash-chromatography on silica gel (ethyl acetate:methanol=98:2) to yield 2-acetylamino-4-(2-amino-5-chlorophenyl)-N-(2-hydroxy-1-phenyl-ethyl)-4-oxobutyramide as a yellow solid (0.18 g; 22%; m.p. 212°-215° C.) (pure diastereoisomer with Rf<).

Workup

  1. stirringThe reaction was then stirred for 2 h in an ice bath and 16 h at room temperature
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried with an
  6. concentrationsodium sulfate and concentrated to dryness
  7. customThe residue was purified by flash-chromatography on silica gel (ethyl acetate:methanol=98:2)

Sources & evidence

ORD record
ord-b2ade4a69b63473ca2d9cafd1622f01b
Source dataset
uspto-grants-1998_07
Patent number
US05786508

Reaction notes

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