Dicyclohexylcarbodiimide → HCID 53863859, compound

HRID 615699Notes

Reaction equation

HRID 615699 reaction equation
[CH3:1][Si:2]([CH:5](O)[CH3:6])([CH3:4])[CH3:3].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:23][C:24]1[S:25][CH:26]=[C:27]([CH2:29][C:30]([OH:32])=[O:31])[N:28]=1>CN(C)C1C=CN=CC=1.C(#N)C>[NH2:23][C:24]1[S:25][CH:26]=[C:27]([CH2:29][C:30]([O:32][CH2:6][CH2:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[O:31])[N:28]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 34665(2-Amino-1,3-thiazol-4-yl)acetic acidHCID 124478981-(Trimethylsilyl)ethanol

Product 1

HCID 53863859HCID 53863859, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

11.2 g (15.8 ml, 0.1 mol) of trimethylsilylethanol, 100 mg of 4-dimethylaminopyridine and 11.4 g of dicyclohexylcarbodiimide are added at room temperature to 7.9 g (0.05 mol) of 2-aminothiazol-4-ylacetic acid in 50 ml of acetonitrile and the mixture is stirred for 2 days. The precipitated urea is then filtered off under suction, washed with ether, the washings are concentrated on a rotary evaporator and the residue is taken up in ether and the ethereal solution is washed with 0.5N hydrochloric acid and with NaHCO3 solution, dried over MgSO4 and concentrated on a rotary evaporator. After concentration of the solution and addition of petroleum ether, the desired ester crystallizes out.

Workup

  1. filtrationThe precipitated urea is then filtered off under suction
  2. washwashed with ether
  3. concentrationthe washings are concentrated on a rotary evaporator
  4. washthe ethereal solution is washed with 0.5N hydrochloric acid and with NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated on a rotary evaporator
  7. additionAfter concentration of the solution and addition of petroleum ether
  8. customthe desired ester crystallizes out

Sources & evidence

ORD record
ord-e597ff69466c451ab89eef0a25a88946
Source dataset
uspto-grants-1985_02
Patent number
US04500716

Reaction notes

Loading…