Sodium Hydroxide → HCID 20475779, compound

HRID 903422Notes

Reaction equation

HRID 903422 reaction equation
C(OC([N:8]([C:23]1[CH:35]=[CH:34][C:26]([C:27](N2C=CN=C2)=[O:28])=[CH:25][CH:24]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=O)(C)(C)C.[OH-].[Na+].[NH2:38][CH2:39][CH:40]([OH:43])[CH2:41][OH:42]>C(Cl)(Cl)Cl>[CH:17]1([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:23]2[CH:35]=[CH:34][C:26]([C:27]([NH:38][CH2:39][CH:40]([OH:43])[CH2:41][OH:42])=[O:28])=[CH:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 735613-Amino-1,2-propanediolHCID 20475773HCID 20475773, compound

Product 1

HCID 20475779HCID 20475779, 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-(8-cyclohexyloctyl)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. in 50 ml. of anhydrous trifluoroacetic acid. The solvent is again evaporated and the oil is crystallized from acetone to yield light yellow crystals of the product.

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
  7. customto yield light yellow crystals of the product

Sources & evidence

ORD record
ord-dcaa2d8df4ed4c9d81cc99aba65b2d69
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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