Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,4,6-Trichlorobenzenesulfonyl chloride | HCID 521335 | — |
| Reactant | HCID 71468935 | HCID 71468935 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71468675 | HCID 71468675 | 66.2% |
Reaction Steps
To a solution of di-tert-butyl (4S)-4-(3-hydroxypropyl)-N-trityl-L-glutamate (438 mg, 0.78 mmol) and triethylamine (327 μL, 2.35 mmol) in dichloromethane (7.0 mL) was added 2,4,6-trichlorobenzenesulfonyl chloride (328.6 mg, 1.17 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and then water was added. The organic layer was separated, and aqueous layer was extracted with dichloromethane. Combined organic solution was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (ethyl acetate/n-hexane=10/90) to give the desired product (415 mg, 66%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09000037B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-56cf7bbd43a4424d88f2420d70264232 |
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| Source note | uspto-grants-2015_04 |
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