HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2120496Generated: October 26, 2026
Dimethylformamide → (R)-N-[1-[(hydroxyamino)carbonyl]-2-methylpropyl]-1-(4-methylphenyl)cyclopropanecarboxamide
https://huagongshe.com/reaction/2120496
Participants
| Role | Name | HCID | Charge |
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| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-(p-Tolyl)cyclopropanecarboxylic acid | HCID 98639 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Product | (R)-N-[1-[(hydroxyamino)carbonyl]-2-methylpropyl]-1-(4-methylphenyl)cyclopropanecarboxamide | HCID 9882466 | 52% |
Reaction Steps
N,N-diisopropylethylamine (0.539 mL, 4 eq) was added to a mixture of the crude amine hydrochloride (200 mg) from reaction (1b), 1-(4-methylphenyl)-1-cyclopropane carboxylic acid (163 mg, 1.2 eq) and HATU (441 mg, 1.5 eq) in N,N-dimethylformamide (1 mL). The mixture was stirred at room temperature overnight and at 70° C. for 90 min. Following addition of ethyl acetate (100 mL), the mixture was washed with 1:1 mixture of 1 N hydrochloric acid-saturated brine (2×10 mL), dried (MgSO4) and concentrated. Silica gel column chromatography (ethyl acetate-hexane, 40:60) yielded the desired product (127 mg, 52% for two steps). MS found: (M+H)+=381.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06689771B2 |
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| Source dataset | uspto-grants-2004_02 |
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| ORD ID | ord-cf0be98f34a648519716df54b357a4d2 |
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| Source note | uspto-grants-2004_02 |
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