Methanol → HCID 19790260, compound

HRID 905408Notes

Reaction equation

[OH-].[Na+].[C:3]([NH:22][C:23]1[N:24]=[N:25][N:26]([CH2:28][C:29]([O:31]CC)=[O:30])[N:27]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO.C(OC(C)C)(C)C>O1CCCC1>[C:3]([NH:22][C:23]1[N:24]=[N:25][N:26]([CH2:28][C:29]([OH:31])=[O:30])[N:27]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To an aqueous solution (27 ml) of sodium hydroxide (2.1 g) were added ethyl 2-(5-tritylamino-2H-tetrazol-2-yl)acetate (14.2 g), methanol (50 ml) and tetrahydrofuran (100 ml), and the mixture was stirred at 40° C. for 2 hours. After the organic solvent was removed by evaporation, to the residue were added water (50 ml) and ethyl acetate (50 ml), followed by separating out the aqueous layer. Thereto was added ethyl acetate (100 ml) and then adjusted to pH 1.5 with 10% hydrochloric acid. The aqueous solution was washed with an aqueous sodium chloride (50 ml) and dried over magnesium sulfate. Removal of the solvent gave a residue, which was pulverized with diisopropyl ether to obtain 2-(5-tritylamino-2H-tetrazol-2-yl)acetic acid (9.0 g).

Workup

customAfter the organic solvent was removed by evaporation, to the residue
additionwere added water (50 ml) and ethyl acetate (50 ml)
customby separating out the aqueous layer
additionThereto was added ethyl acetate (100 ml)
washThe aqueous solution was washed with an aqueous sodium chloride (50 ml)
dry with materialdried over magnesium sulfate
customRemoval of the solvent
customgave a residue, which

Sources & evidence

ORD record: ord-538923f840754c899c9dadb28be35a49
Source dataset: uspto-grants-1983_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04423213

Reaction notes

Loading…