m-Chloroperbenzoic acid → di-tert-Butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)-1-oxidopyridin-2-yl]methyl}-L-glutamate

HRID 591308Notes

Reaction equation

HRID 591308 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][F:29])=[CH:22][N:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:42]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][F:29])=[CH:22][N+:21]=1[O-:42])[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70674548Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}-L-glutamate

Product 1

HCID 117812666di-tert-Butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)-1-oxidopyridin-2-yl]methyl}-L-glutamateYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 350 mg di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}-L-glutamate (0.68 mmol; see Example 17d) in dichloromethane (5 mL) was added 185 mg meta-chloro peroxybenzoic acid (70%), and the mixture was stirred for 1 h at room temperature. The mixture was extracted with aqueous sodium bicarbonate, followed by re-extraction of the aqueous layer with dichloromethane. The combined organic layers were concentrated in vacuo, and the residue was purified by preparative HPLC (Method D) to give 340 mg of the target compound (93% yield).

Workup

  1. extractionThe mixture was extracted with aqueous sodium bicarbonate
  2. extractionfollowed by re-extraction of the aqueous layer with dichloromethane
  3. concentrationThe combined organic layers were concentrated in vacuo
  4. customthe residue was purified by preparative HPLC (Method D)

Sources & evidence

ORD record
ord-108fbad314594c09b4ad8cdc8c1f2177
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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