Hydrochloric Acid → Methyl 2-(((benzyloxy)carbonyl)amino)acetimidate

HRID 445397Notes

Reaction equation

HRID 445397 reaction equation
[NH2:1][C:2](=[O:15])[CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.F[B-](F)(F)F.[CH3:21][O+](C)C.Cl>C(Cl)Cl>[CH2:7]([O:6][C:5]([NH:4][CH2:3][C:2](=[NH:1])[O:15][CH3:21])=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70366Phenylmethyl N-(2-amino-2-oxoethyl)carbamateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)

Product 1

HCID 66822280Methyl 2-(((benzyloxy)carbonyl)amino)acetimidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl (2-amino-2-oxoethyl)carbamate (8.5 g, 40.8 mmol) in CH2Cl2 (204 mL) was added trimethyloxonium tetrafluoroborate (6.0 g, 40.8 mmol) in one portion. The resulting mixture was stirred for 24 h, then acidified to pH˜3 with 1N ethereal HCl. The resulting mixture was concentrated under reduced pressure to yield methyl 2-(((benzyloxy)carbonyl)amino)acetimidate. A solution of methyl 2-(((benzyloxy)carbonyl)amino)acetimidate (9.3 g, 36 mmol), 4-(benzyloxy)benzothiohydrazide (8.0 g, 24 mmol) and diisopropylethylamine (4.2 mL, 24 mmol) in methanol (480 mL) was refluxed for 12 h. The resulting mixture was cooled to room temperature, at which point benzyl ((5-(4-(benzyloxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate precipitated and was collected (MS m/z=432 MH+).

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-deced21729c74026be77b41c6fbc3276
Source dataset
uspto-grants-2013_07
Patent number
US08476302B2

Reaction notes

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