2-Methyl-6-nitrobenzoic anhydride → HCID 86701314, compound

HRID 1627044Notes

Reaction equation

HRID 1627044 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][O:17][CH2:18][C@H:19]([O:34][CH2:35][C:36]([CH3:38])=[CH2:37])[C@@H:20]([O:29][CH2:30][C:31]([CH3:33])=[CH2:32])[C@H:21]([OH:28])[CH2:22][O:23][CH2:24][C:25]([CH3:27])=[CH2:26])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC=C([N+]([O-])=O)C=1C(OC(C1C([N+]([O-])=O)=CC=CC=1C)=O)=O>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:38][C:36](=[CH2:37])[CH2:35][O:34][C@@H:19]1[C@@H:20]([O:29][CH2:30][C:31]([CH3:33])=[CH2:32])[C@@H:21]([CH2:22][O:23][CH2:24][C:25]([CH3:27])=[CH2:26])[O:28][C:13](=[O:15])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:16][O:17][CH2:18]1.[CH3:38][C:36](=[CH2:37])[CH2:35][O:34][C@@H:19]1[C@@H:20]([O:29][CH2:30][C:31]([CH3:33])=[CH2:32])[C@@H:21]([CH2:22][O:23][CH2:24][C:25]([CH3:27])=[CH2:26])[O:28][C:13](=[O:14])[C@H:12]([NH:11][C:9](=[O:10])[O-:8])[CH2:16][O:17][CH2:18]1

Participants

6

Reactant 2

HCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 86701317HCID 86701317, compound

Product 2

HCID 86701314HCID 86701314, compoundYield 36%HCID 86701315HCID 86701315, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of (S)-2-(benzyloxycarbonylamino)-3-((2S,3S,4R)-4-hydroxy-2,3,5-tris(2-methylallyloxy)pentyloxy)propanoic acid (400 mg, 0.747 mmol) in anhydrous toluene (400 mL) was added to a solution of MNBA (411 mg, 1.195 mmol) and DMAP (547 mg, 4.48 mmol) in toluene (1600 mL) over the course of 3 h via syringe pump. After the addition was complete, the reaction mixture was stirred for 1 h, concentrated, and the residue purified by flash chromatography (SiO2, 20% EtOAc/hexanes) to furnish benzyl (3S,7S,8R,9R)-7,8-bis(2-methylallyloxy)-9-((2-methylallyloxy)methyl)-2-oxo-1,5-dioxonan-3-ylcarbamate (140 mg, 36%) and (3R,7S,8R,9R)-7,8-bis(2-methylallyloxy)-9-((2-methylallyloxy)methyl)-2-oxo-1,5-dioxonan-3-ylcarbamate as white foams (140 mg, 36%).

Workup

  1. additionAfter the addition
  2. concentrationconcentrated
  3. customthe residue purified by flash chromatography (SiO2, 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2d32c519ff4247c49a32850f7485d68d
Source dataset
uspto-grants-2014_07
Patent number
US08785479B2

Reaction notes

Loading…