Water → tert-Butyl [(3-bromo-4,5-dihydro-1,2-oxazol-5-yl)methyl]carbamate

HRID 1651730Notes

Reaction equation

HRID 1651730 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]=[CH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].O.[Br:18][C:19](Br)=[N:20][OH:21]>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[O:21][N:20]=[C:19]([Br:18])[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromideHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamate

Product 1

HCID 13637723tert-Butyl [(3-bromo-4,5-dihydro-1,2-oxazol-5-yl)methyl]carbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-tert-butoxycarbonyl allyl amine, 20 gm, in 700 ml of ethyl acetate and containing 65 gm of NaHCO3 and 50 ml of water, was added portion-wise 80 gm of dibromoformaldoxime at room temperature with vigorous stirring. After completion of the reaction, the organic portion was washed with water (2×100 ml), 100 ml each of 5% NaHCO3, brine and dried over anh. MgSO4 and concentrated to give an oil. Purification by chromatography on silica gel gave the desired product as an oil which solidified on standing. IR(KBr): 3322, 2988, 1680, 1529 cm-1. 1H NMR (80 MHz, CDCl3): delta 1.45 (s, 9H, t-butyl), 2.8-3.5 (m, 4H, CH2CHO, CH2N), 4.6-5.1 (broad s, superimposed on a multiplet, 2H, NH, CHO).

Workup

  1. customAfter completion of the reaction
  2. washthe organic portion was washed with water (2×100 ml), 100 ml each of 5% NaHCO3, brine
  3. dry with materialdried over anh. MgSO4
  4. concentrationconcentrated
  5. customto give an oil
  6. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-0aefa1dbb7ff43a4b4234b07327de9ed
Source dataset
uspto-grants-1990_05
Patent number
US04929630

Reaction notes

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