Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | tert-Butyl [(2S,4S)-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-5-methyl-1-oxohexan-2-yl]carbamate | HCID 11590225 | — |
| Product | HCID 101747281 | HCID 101747281 | — |
Reaction Steps
The reaction mixture is stirred for a further 20 minutes at 55° C. and then cooled to 5° C. A solution of 2(S)-(tert-butoxycarbonyl)amino-4(S)-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-5-methyl-hexanal (190 g) in tetrahydrofuran (700 ml) is then added dropwise. The reaction mixture is stirred for a further 3 hours at room temperature, then at 5° C. saturated ammonium chloride solution is added and the mixture is extracted with diethyl ether. The organic phases are concentrated and purified by FC (4 kg of silica gel, ethyl acetate/hexane 1:3). The title compound is obtained in the form of a colourless oil (139 g): Rf (ethyl acetate/hexane 1:2)=0.26; HPLC Rt =22.7 and 22.8 min ((4:6)-diastereoisomeric mixture).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05659065 |
|---|
| Source dataset | uspto-grants-1997_08 |
|---|
| ORD ID | ord-bfb90797dc9b4900b4c445295340c58f |
|---|
| Source note | uspto-grants-1997_08 |
|---|