Sodium Hydroxide → HCID 21163300, compound

HRID 904265Notes

Reaction equation

HRID 904265 reaction equation
C(OC([N:8]([C:28]1[CH:40]=[CH:39][C:31]([C:32](N2C=CN=C2)=[O:33])=[CH:30][CH:29]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=O)(C)(C)C.[OH-].[Na+].[NH2:43][CH2:44][CH:45]([OH:48])[CH2:46][OH:47]>C(Cl)(Cl)Cl>[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:28]1[CH:40]=[CH:39][C:31]([C:32]([NH:43][CH2:44][CH:45]([OH:48])[CH2:46][OH:47])=[O:33])=[CH:30][CH:29]=1)([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 735613-Amino-1,2-propanediolHCID 21163326HCID 21163326, compound

Product 1

HCID 21163300HCID 21163300, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture containing 4.3 g. of 1-{4-[N-(t-butyloxycarbonyl)-N-(15-carbomethoxypentadecyl)amino]benzoyl}imidazole, 50 ml. of chloroform, and 50 ml. of 5 N sodium hydroxide is added 1.1 g. of 3-amino-1,2-propanediol. The solution is vigorously stirred for 24 hours, the layers are separated, and the chloroform solution is washed once with 50 ml. of 1 N sodium hydroxide. The solvent is evaporated and the residue is heated for 30 minutes at 40° C. and 50 ml. of anhydrous trifluoroacetic acid. The solvent is again evaporated and the oil is crystallized from acetone to yield the product as a light yellow crystalline solid.

Workup

  1. additionTo a mixture containing 4.3 g
  2. customthe layers are separated
  3. washthe chloroform solution is washed once with 50 ml
  4. customThe solvent is evaporated
  5. customThe solvent is again evaporated
  6. customthe oil is crystallized from acetone

Sources & evidence

ORD record
ord-81644796679b42b794e662becd5996ab
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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