HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → 2-Hydroxy-2,4-dimethyl-3-pentanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | 3-Amino-2,4-dimethylpentan-2-ol | HCID 13247948 | — |
| Reactant | N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-alanine | HCID 53966575 | — |
| Catalyst | Dihydroxy(dioxo)molybdenum;phosphonic acid | HCID 21863154 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | 2-Hydroxy-2,4-dimethyl-3-pentanone | HCID 547735 | — |
Reaction Steps
To a solution of 2.14 g. (5.0 mmole) beta-benzyl-N-benzyloxycarbonyl-L-aspartyl-D-alanine in 35 ml. tetrahydrofuran cooled to -15° was added 0.55 ml. (5.0 mmole) N-methylmorpholine and 0.48 ml. (5.0 mmole) ethyl chloroformate. The mixture was stirred at -15° to -10° C. for two minutes and 0.66 g. (5.0 mmole) 3-amino-2-hydroxy-2,4-dimethylpentane was added. The mixture was allowed to warm to room temperature, stirred overnight and worked-up as described in Example 5, Part B, to obtain the diprotected dipeptide amide, Rf 0.27 (TLC, ethyl acetate/hexane, 1:1, phosphomolybdic acid spray, heat) which was used directly in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04894464 |
| Source dataset | uspto-grants-1990_01 |
| ORD ID | ord-079a054ae14c446cae2a98d5a52d1fe9 |
| Source note | uspto-grants-1990_01 |