Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Pentanoyl chloride, 4-methyl- | HCID 170008 | — |
| Reactant | HCID 15016692 | HCID 15016692 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 56983237 | HCID 56983237 | 100.8% |
Reaction Steps
To (3S,4S)-1-amino-3-hydroxy-4-t-butyloxycarbonylamino-5-cyclohexylpentane (30.8 mg, 0.102 mmol) in dry methylene chloride (3 mL) at 0° C. was added 4-methylpentanoyl chloride (17.0 microliters, 0.123 mmol) and triethylamine (20.0 microliters, 0.143 mmol). The mixture was stirred at 0° C. for 1 hour, evaporated, taken up in methanol (3 mL) and treated with 1M NaOH (1 mL). After stirring for 1 hour, the mixture was diluted with ether, washed sequentially with 0.5M H3PO4, saturated NaHCO3 solution, and brine, and then dried over Na2SO4 and evaporated to afford 41.0 mg (100%) of the desired product as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04857507 |
|---|
| Source dataset | uspto-grants-1989_08 |
|---|
| ORD ID | ord-e61e62aed9ea4f3b8ab836946be2d6e7 |
|---|
| Source note | uspto-grants-1989_08 |
|---|