HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-({[4-ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyl Formate | HCID 61207 | — |
| Reactant | 4-Ethyl-3-(3-methoxypropoxy)benzoic acid | HCID 57355538 | — |
| Reactant | (3S*,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 131728361 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | (3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-({[4-ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 131728364 | — |
Reaction Steps
From (3S,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (8.5 g, 22 mmol), 4-ethyl-3-(3-methoxy-propoxy)-benzoic acid (5.76 g, 24.2 mmol), BOPCI (6.16 g, 24.2 mmol) and triethylamine (12.3 g, 88 mmol). TLC, Rf (CH2Cl2/MeOH 95:5)=0.32. tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 8.81 min. MS (LC-MS): [M+H-BOC]+507.3
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807709B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-e7ca5b31cb0f48a09f5577b7148ddd58 |
| Source note | uspto-grants-2010_10 |