Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bromomethyl acetate | HCID 68536 | — |
| Reactant | HCID 67972391 | HCID 67972391 | — |
| Product | HCID 86705129 | HCID 86705129 | 14.5% |
Reaction Steps
Bromomethyl acetate (15.3 mg, 100 μmol) was added to a solution of (R)-3-[N-(2′,5′-dichlorobiphenyl-4-ylmethyl)-N′-(1-hydroxy-1H-1,2,3-triazole-4-carbonyl)hydrazino]-2-hydroxypropionic acid (31.2 mg, 66.8 μmol) in acetone (0.5 mL, 6.8 mmol) followed by Et3N (18.6 μL, 134 μmol). The resulting mixture was stirred at 55° C. for 1 hour. The mixture was then concentrated in vacuo to yield a yellow liquid. The crude liquid was purified (preparative scale C18 column chromatography, small column, using 30-90% MeCN in water with 0.05% TFA) to yield the title compound (5.2 mg, purity 96%) as a white solid. MS m/z [M+H]+ calc'd for C22H21Cl2N5O2, 538.08. found 538.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08871792B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-6761e5bb7020426f826afa03985edb3c |
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| Source note | uspto-grants-2014_10 |
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