Sodium Hydroxide → HCID 20549386, compound

HRID 1659931Notes

Reaction equation

HRID 1659931 reaction equation
C(OC([N:8]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([F:40])([F:39])[F:38])[C:9]1[CH:21]=[CH:20][C:12]([C:13](C2N=CNC=2)=[O:14])=[CH:11][CH:10]=1)=O)(C)(C)C.[OH-].[Na+].[NH2:43][CH2:44][CH:45]([OH:48])[CH2:46][OH:47]>C(Cl)(Cl)Cl>[OH:48][CH:45]([CH2:46][OH:47])[CH2:44][NH:43][C:13](=[O:14])[C:12]1[CH:11]=[CH:10][C:9]([NH:8][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([F:38])([F:39])[F:40])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 735613-Amino-1,2-propanediolHCID 178453379HCID 178453379, compound

Product 1

HCID 20549386HCID 20549386, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture containing 4.3 g. of 1-{4-[N-(tert-butyloxycarbonyl)-4-[15-(trifluoromethyl)pentadecylamino]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. in 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 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-b351fe34fe06432a97a21c8d4ce5b9af
Source dataset
uspto-grants-1981_12
Patent number
US04305959

Reaction notes

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