HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 90412289, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyano-borohydride | HCID 498716 | — |
| Reactant | 2-((Tert-butyldimethylsilyl)oxy)acetaldehyde | HCID 4187788 | — |
| Reactant | HCID 90412361 | HCID 90412361 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 90412289 | HCID 90412289 | — |
Reaction Steps
To a solution of Example 59F (50 mg, 0.130 mmol) in dichloromethane (1 mL)/methanol (1 mL) was added triethylamine (0.036 mL, 0.260 mmol) followed by acetic acid (0.037 mL, 0.651 mmol) and (t-butyldimethylsilyloxy)acetaldehyde (0.050 mL, 0.260 mmol). After stirring for 5 minutes, MP-cyanoborohydride (2.49 mmol/g, 209 mg, 0.52 mmol) was added and the mixture was shaken for 16 hours at room temperature. The resin was filtered off, and washed with methanol/dichloromethane (2×3 mL). The crude mixture was concentrated and used in the next step without further purification. LCMS: 470.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09073922B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-110365567a4f4a52955b2a2d4260c2e1 |
| Source note | uspto-grants-2015_07 |