Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | (4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride | HCID 44541812 | — |
| Reactant | HCID 67074149 | HCID 67074149 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67074072 | HCID 67074072 | — |
Reaction Steps
To 0.15 g (0.3 mmol) of (S)-4-(3-tert-butoxycarbonyl-propyl)-6-methyl-5-oxo-piperazine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester in 5 ml of THF was added 1.5 ml of 37% hydrochloric acid. The reaction was stirred for 2 h after which time it was evaporated to dryness. The residue was redissolved in 2 m of DMF, 0.14 g (0.4 mmol) of HATU and 0.06 g (0.4 mmol) of (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (intermediate 2) were added followed by 0.2 ml (1.2 mmol) of triethylamine. The reaction was stirred for 1 h after which time the solvent was evaporated, the residue redissolved in EtOAc, washed with water, brine, dried (Na2SO4) and concentrated to give after flash silica gel column (CH2Cl2/MeOH 95:5) the title compound in quantitative yield as a colorless foam. MS: 502.4 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08445674B2 |
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| Source dataset | uspto-grants-2013_05 |
|---|
| ORD ID | ord-5a34847871674af296f804267179eb0e |
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| Source note | uspto-grants-2013_05 |
|---|
