HCID 19036264, compound → HCID 178468947, compound

HRID 53015Notes

Reaction equation

HRID 53015 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([S:52][CH3:53])[N:8]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH3:4])[CH3:3]>C(O)(=O)C>[OH:1][C:2]([C:5]1[N:6]=[C:7]([S:52][CH3:53])[N:8]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 19036264HCID 19036264, compound

Product 1

HCID 178468947HCID 178468947, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

900 mg of ethyl 4-(1-hydroxy-1-methylethyl)-2-methylthio-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}metylimidazole-5-carboxylate [prepared as described in step (a) above] were added to 10 ml of a 25% v/v aqueous solution of acetic acid, and the mixture was stirred at 60° C. for 1 hour. At the end of this time, the reaction mixture was cooled, and the crystals of trityl alcohol which appeared were filtered off. These crystals were washed with a 50% v/v aqueous solution of acetic acid, and the filtrate and the washings were mixed. The resulting mixture was concentrated by evaporation under reduced pressure, and the resulting residue was crystallized from ethyl acetate, to give 529 mg of the title compound as crystals, melting at 209°-210° C.

Workup

  1. temperatureAt the end of this time, the reaction mixture was cooled
  2. filtrationthe crystals of trityl alcohol which appeared were filtered off
  3. washThese crystals were washed with a 50% v/v aqueous solution of acetic acid
  4. additionthe filtrate and the washings were mixed
  5. concentrationThe resulting mixture was concentrated by evaporation under reduced pressure
  6. customthe resulting residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a88bbfb02c474b70bab5f87a14b64923
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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