HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-(4-{(1E)-4-[9-(aminoacetyl)-2,9-diazaspiro[5.5]undec-2-yl]but-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside dihydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | tert-butyl[2-(2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undec-9-yl)-2-oxoethyl]carbamate | HCID 131731669 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(4-{(1E)-4-[9-(aminoacetyl)-2,9-diazaspiro[5.5]undec-2-yl]but-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside dihydrochloride | HCID 86762541 | 99.7% |
Reaction Steps
A mixture of tert-butyl[2-(2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undec-9-yl)-2-oxoethyl]carbamate (12.10 g, 13.09 mmoles), dichloromethane (121.00 mL), and hydrogen chloride (4M in 1,4-dioxane; 16.37 mL, 65.47 mmoles) is stirred at ambient temperature for 4 hours. The mixture is concentrated under reduced pressure to provide the title compound (11.70 g; 99.6% yield). Mass spectrum (m/z): 824 (M+1 for free base).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08785404B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-a6e4927e5bf7402fbd412c9929e30476 |
| Source note | uspto-grants-2014_07 |