Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | N-alpha-t-Butyloxycarbonyl-S-(4-methyl-benzyl)-L-cysteine | HCID 7010551 | — |
| Reactant | (2R,3R)-2-aminobutane-1,3-diol hydrochloride | HCID 122236265 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | BOC-Cys(MBzl)-Thr-ol | HCID 131713414 | — |
Reaction Steps
2.1 ml N-methylmorpholine are added with stirring to a solution of 6.3 g Boc-Cys(MBzl)-OH in 50 ml THF, followed by drop-wise addition at -15° C. of 2.4 ml chloroformic acid isobutyl ester. After stirring for 5 minutes at -15° C. a solution of 3.3 g H-Thr-ol hydrochloride and 4.1 ml N-methylmorpholine in 30 ml DMF, pre-cooled to -10° C. is added. The reaction mixture is stirred for 2 hrs. at 0° C. and for a further 2 hrs. at room-temperature. 50 ml 10% KHCO3 -solution are added and the whole concentrated under vacuum. After dilution with AcOEt, washing 3× with 2 N citric acid, 3× with KHCO3 -solution and 1× with NaCl solution, the organic phase is dried over Na2SO4 and evaporated under vacuum to yield the title compound:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04435385 |
|---|
| Source dataset | uspto-grants-1984_03 |
|---|
| ORD ID | ord-7e91228172af46a2830e18e4f7934b6f |
|---|
| Source note | uspto-grants-1984_03 |
|---|
