HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → tert-butyl (1S)-1-{[methoxy(methyl)amino]carbonyl}pentylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | N-tert-Butoxycarbonyl-L-norleucine | HCID 2733747 | — |
| Product | tert-butyl (1S)-1-{[methoxy(methyl)amino]carbonyl}pentylcarbamate | HCID 10061913 | — |
Reaction Steps
2(S)-(tert-Butoxycarbonylamino)hexanoic acid (24.6 g, 0.106 mol), N,O-dimethylhydroxylamine hydrochloride (15.5 g, 0.15 mol), EDC hydrochloride (22.3 g, 0.117 mol) and HOBT (14.3 g, 0.106 mol) were stirred in dry, degassed DMF (300 mL) at 20° C. under nitrogen. N-Methylmorpholine was added to obtain pH 7. The reaction was stirred overnight, the DMF distilled under high vacuum, and the residue partitioned between ethyl acetate and 2% potassium hydrogen sulfate. The organic phase was washed with saturated sodium bicarbonate, water, and saturated brine, and dried with magnesium sulfate. The solvent was removed in vacuo to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06060038 |
| Source dataset | uspto-grants-2000_05 |
| ORD ID | ord-23b24502bfc64557b8a709a145d9f6d1 |
| Source note | uspto-grants-2000_05 |