HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tri-o-tolylphosphine → tert-Butyl (3R)-3-(tert-butoxycarbonylamino)-4-[5-(hydroxymethyl)-2-nitro-phenyl]butanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | (3-Bromo-4-nitrophenyl)methanol | HCID 53414436 | — |
| Reactant | tert-Butyl (S)-3-(Boc-amino)-4-iodobutanoate | HCID 86222841 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Product | tert-Butyl (3R)-3-(tert-butoxycarbonylamino)-4-[5-(hydroxymethyl)-2-nitro-phenyl]butanoate | HCID 118276599 | — |
Reaction Steps
Following the General Procedure of Description 15 (Part A), the zinc insertion product of (6c) is used in situ to cross couple with commercial (3-bromo-4-nitro-phenyl)methanol (232 mg, 1.0 mmol) in the presence of tris(benzylideneacetone)dipalladium (Pd2(dba)3) (23 mg, 0.025 mmol, 2.5 mol-%) and tris(o-tolyl)phosphine (P(o-tol)3) (30 mg, 0.10 mmol, 10 mol-%) in anhydrous degassed DMF (3 mL). Filtration, aqueous work-up, and purification by silica gel column chromatography furnish the title compound (20a).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09394237B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-5107d489a8344ff29237d7b0c6160c6c |
| Source note | uspto-grants-2016_07 |