Water → HCID 57535349, compound

HRID 1455579Notes

Reaction equation

HRID 1455579 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]([CH2:19][CH3:20])[CH:9]([O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][N+:11]([O-:13])=O)([CH3:4])([CH3:3])[CH3:2].C1(N=C=O)C=CC(N=C=O)=CC=1.[CH3:34][CH:35]([CH3:38])[C:36]#[CH:37].O>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]([CH:9]([C:10]1[CH:37]=[C:36]([CH:35]([CH3:38])[CH3:34])[O:13][N:11]=1)[O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH2:19][CH3:20])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 610091,4-DiisocyanatobenzeneHCID 690193-Methylbut-1-yneHCID 57535331HCID 57535331, compound

Product 1

HCID 57535349HCID 57535349, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (1-Ethyl-3-nitro-2-trimethylsilanyloxy-propyl)-carbamic acid tert-butyl ester (918 mg, 2.86 mmol), 1,4-Phenylene diisocyanate (1.38 g, 8.5 mmol) and 3-methyl-1-butyne (586 mg, 8.5 mmol) in dry toluene (15 mL) under N2 is added triethylamine (10 drops). The mixture is heated to 50° C. in a sealed vial for 28 h, and then cooled to room temperature Water (1 mL) is added and the mixture is stirred for an additional 2 h, then filtered. The filtrate is concentrated in vacuum and the residue is purified over 35 g silica gel, eluted with ethyl acetate: heptane (1:5) to afford {1-[(5-Isopropyl-isoxazol-3-yl)-trimethylsilanyloxy-methyl]-propyl}-carbamic acid tert-butyl ester (764 mg, 72%) as an oil.

Workup

  1. additionis added
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated in vacuum
  4. customthe residue is purified over 35 g silica gel
  5. washeluted with ethyl acetate: heptane (1:5)

Sources & evidence

ORD record
ord-d029dcc7bd4a430dab5e7ea47d9c7f02
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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