Water → HCID 178440072, compound

HRID 2210567Notes

Reaction equation

O.[OH:2][C:3]([C:6]1[N:7]=[C:8]([CH2:54][CH2:55][CH3:56])[N:9]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:48](=[O:53])[C:49]([O:51][CH3:52])=[O:50])=[CH:38][CH:37]=2)[C:10]=1[C:11]1[N:12]=[N:13][N:14](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:15]=1)([CH3:5])[CH3:4]>C(O)(=O)C>[OH:2][C:3]([C:6]1[N:7]=[C:8]([CH2:54][CH2:55][CH3:56])[N:9]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:48](=[O:53])[C:49]([O:51][CH3:52])=[O:50])=[CH:40][CH:41]=2)[C:10]=1[C:11]1[NH:15][N:14]=[N:13][N:12]=1)([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

1.5 ml of water were added to a solution of 527 mg of methyl {4'-[4-(1-hydroxy-1-methylethyl)-2-propyl-5-(2-trityltetrazol-5-yl)imidazol-1-ylmethyl]biphenyl-2-yl}glyoxylate [prepared as described in step (a) above] dissolved in 3.5 ml of acetic acid, and the resulting mixture was stirred at 70° C. for 1.5 hours. At the end of this time, 2 ml of water were added to the mixture. The resulting mixture was ice-cooled, and then the precipitate was removed by filtration. The filtrate was concentrated by evaporation under reduced pressure, and the residual acetic acid was removed by azeotropic distillation with toluene, to give 206 mg of the title compound, as crystals melting at 131°-132° C. (after crystallization from a mixture of diethyl ether and ethyl acetate).

Workup

temperaturecooled
customthe precipitate was removed by filtration
concentrationThe filtrate was concentrated by evaporation under reduced pressure
customthe residual acetic acid was removed by azeotropic distillation with toluene

Sources & evidence

ORD record: ord-aa3b54799f48483fad12b7bf6ae9f9d8
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05459148

Reaction notes

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