HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilyl isocyanate → (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilyl isocyanate | HCID 70696 | — |
| Reactant | (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine | HCID 69427603 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid amide | HCID 69431348 | 47% |
Reaction Steps
A solution of 400 mg (0.86 mmol) (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine in 15 ml CH2Cl2 with 0.3 ml (2.2 mmol) trimethylsilylisocyanate and a catalytic amount of DMAP was stirred over night. The reaction was extracted with aqueous 10% KHSO4/EtOAc (3×) and the organic phase was dried over Na2SO4. Crystallization (CH2Cl2/MeOH/Et2O) gave 205 mg (47%) (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid amide, MS: 509 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07189756B2 |
| Source dataset | uspto-grants-2007_03 |
| ORD ID | ord-86693f6621594f34a5d07850a3cd3391 |
| Source note | uspto-grants-2007_03 |