HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2075524Generated: October 26, 2026
4-Chloro-1-hydroxy-2-naphthoic acid → 2-[(4-Chloro-1-hydroxy-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid tert-butyl ester
https://huagongshe.com/reaction/2075524
Participants
| Role | Name | HCID | Charge |
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| Reactant | 4-Chloro-1-hydroxy-2-naphthoic acid | HCID 79416 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | Tert-butyl 2-amino-2-methylpropanoate hydrochloride | HCID 12186776 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[(4-Chloro-1-hydroxy-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid tert-butyl ester | HCID 66701166 | 28% |
Reaction Steps
2.25 g of 4-chloro-1-hydroxy-naphthalene-2-carboxylic acid, 3.57 2-amino-2-methyl-propionic acid tert-butyl ester hydrochloride, 6.93 g HATU and 5.29 mL of N,N′diisopropylethylamine were dissolved in 100 mL of dimethylformamide. The reaction was heated at 60° C. for 1.5 hour followed by room temperature overnight. Water was added and the mixture was extracted with diethyl ether twice. The combined organic layers were dried with magnesium sulfate and concentrated in vacuo. Purification by flash chromatography on silica with heptanes/ethyl acetate afforded 1.016 g (28%) of 2-[(4-chloro-1-hydroxy-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid tert-butyl ester as a beige solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07919628B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-902e579a38af4a4d8a3cdd85eadb0b04 |
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| Source note | uspto-grants-2011_04 |
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