Phenyl isocyanate → HCID 86591185, compound

HRID 2417412Notes

Reaction equation

HRID 2417412 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C@H:7]2[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[N:8]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:4][CH:3]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[NH:29]([C:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@H:7]2[CH2:11][O:10][C:9]([CH3:12])([CH3:13])[N:8]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:21][CH:22]=1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 86591186HCID 86591186, compound

Product 1

HCID 86591185HCID 86591185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of tert-butyl (S)-4-(4-aminobenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.0 g) in dichloromethane (10 ml) was added dropwise phenyl isocyanate (0.39 ml). The mixture was stirred at the same temperature for 1 hour and partitioned between chloroform and saturated sodium bicarbonate solution. The organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give tert-butyl (S)-4-[4-[(anilinocarbonyl)amino]benzyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.48 g) as colorless oil.

Workup

  1. custompartitioned between chloroform and saturated sodium bicarbonate solution
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-281453783337451ca67c5bb81a89dae3
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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