HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1264403Generated: October 30, 2026
Trifluoroacetic acid → (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl-(1H-tetrazol-5-ylmethyl)-amide
https://huagongshe.com/reaction/1264403
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid | HCID 69428772 | — |
| Reactant | [2-(4-methoxy-benzyl)-2H-tetrazol-5-ylmethyl]-methyl-amide | HCID 86758903 | — |
| Product | (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl-(1H-tetrazol-5-ylmethyl)-amide | HCID 178483115 | 57% |
Reaction Steps
A solution of 150 mg (0.19 mmol) of a 1:1 mixture of (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid [1-(4-methoxy-benzyl)-1H- and [2-(4-methoxy-benzyl)-2H-tetrazol-5-ylmethyl]-methyl-amide in 10 ml TFA was treated with 0.3 ml (1.9 mmol) triethylsilane, refluxed for 7 min at 80° C. and evaporated. Crystallization from CH2Cl2/Et2O gave 46 mg (57%) (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl-(1H-tetrazol-5-ylmethyl)-amide, mp: 175 slow dec., MS: 433 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06541638B2 |
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| Source dataset | uspto-grants-2003_04 |
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| ORD ID | ord-affd5dd3860148ed8807b247c9b972a1 |
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| Source note | uspto-grants-2003_04 |
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