1,1'-Carbonyldiimidazole → HCID 60133633, compound

HRID 557456Notes

Reaction equation

HRID 557456 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:35])[C:25]2[CH:30]=[C:29]([N:31]([CH3:33])[CH3:32])[CH:28]=[CH:27][C:26]=2[NH2:34])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].[C:37](N1C=CN=C1)(N1C=CN=C1)=[O:38]>C(#N)C>[CH3:1][O:2][C:3](=[O:36])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[C:24](=[O:35])[C:25]3[C:26](=[CH:27][CH:28]=[C:29]([N:31]([CH3:32])[CH3:33])[CH:30]=3)[NH:34][C:37]2=[O:38])=[CH:21][CH:22]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 25134448HCID 25134448, compound

Product 1

HCID 60133633HCID 60133633, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

There was suspended, in 480 mL of acetonitrile, 47.1 g of 4-{2-amino-5-di-methylamino-benzoylamino}-Nα-(2,6-dichlorobenzoyl)-L-phenylalanine methyl ester synthesized in the foregoing step 1, then 15.9 g of 1,1′-carbonyl-diimidazole (CDI) was added to the suspension and then the mixture was heated at a temperature ranging from 55 to 60° C. for 2.5 hours with stirring. After the completion of the reaction, the mixture was cooled to 5° C. and the resulting crystals were filtered off to thus give 35.6 g of primary crystals. The filtrate and the wash liquid were concentrated to half, then 200 mL of water was added thereto to thus separate out crystals, the resulting slurry was filtered and the resulting crystals were dried to thus give 6.35 g of secondary crystals. The physical properties of the resulting compound were found to be in good agreement with those observed for the same compound prepared in the foregoing synthesis Example.

Workup

  1. temperaturethe mixture was heated at a temperature
  2. customAfter the completion of the reaction
  3. filtrationthe resulting crystals were filtered off to thus give 35.6 g of primary crystals
  4. concentrationThe filtrate and the wash liquid were concentrated to half
  5. addition200 mL of water was added
  6. customto thus separate out crystals
  7. filtrationthe resulting slurry was filtered
  8. dry with materialthe resulting crystals were dried to thus give 6.35 g of secondary crystals

Sources & evidence

ORD record
ord-ce836f01c50a4276b5879dd197f86063
Source dataset
uspto-grants-2011_11
Patent number
US08058432B2

Reaction notes

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