Tri-o-tolylphosphine → tert-Butyl (3R)-3-(tert-butoxycarbonylamino)-4-[5-(hydroxymethyl)-2-nitro-phenyl]butanoate

HRID 1053665Notes

Reaction equation

HRID 1053665 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:18]I)[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:21]1[CH:22]=[C:23]([CH2:30][OH:31])[CH:24]=[CH:25][C:26]=1[N+:27]([O-:29])=[O:28].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[Zn]>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:18][C:21]1[CH:22]=[C:23]([CH2:30][OH:31])[CH:24]=[CH:25][C:26]=1[N+:27]([O-:29])=[O:28])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 53414436(3-Bromo-4-nitrophenyl)methanolHCID 86222841tert-Butyl (S)-3-(Boc-amino)-4-iodobutanoate

Product 1

HCID 118276599tert-Butyl (3R)-3-(tert-butoxycarbonylamino)-4-[5-(hydroxymethyl)-2-nitro-phenyl]butanoate

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

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).

Workup

  1. customin anhydrous degassed DMF (3 mL)
  2. filtrationFiltration, aqueous work-up, and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-5107d489a8344ff29237d7b0c6160c6c
Source dataset
uspto-grants-2016_07
Patent number
US09394237B2

Reaction notes

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