2,2-Dimethoxypropane → tert-butyl (S)-4-(4-nitrobenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 2417407Notes

Reaction equation

HRID 2417407 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.CO[C:24](OC)([CH3:26])[CH3:25].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[N+:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C@H:3]2[CH2:2][O:1][C:24]([CH3:26])([CH3:25])[N:14]2[C:15]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:21])=[CH:10][CH:9]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 12151763(S)-2-(Boc-amino)-3-(4-nitrophenyl)-1-propanol

Product 1

HCID 86591182tert-butyl (S)-4-(4-nitrobenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl N-[(1S)-2-hydroxy-1-(4-nitrobenzyl)ethyl]carbamate (22.3 g), 2,2-dimethoxypropane (46.3 ml), p-toluenesulfonic acid monohydrate (1.43 g) and dichloromethane (200 ml) was stirred at room temperature for 15 hours. The reaction mixture was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with isopropyl ether to give tert-butyl (S)-4-(4-nitrobenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (16.9 g) as a pale yellow powder.

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-0b291deebc1f47929535dd07a31d3d77
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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