Sodium Hydroxide → HCID 20554714, compound

HRID 1106168Notes

Reaction equation

HRID 1106168 reaction equation
C(OC([N:8]([C:26]1[CH:38]=[CH:37][C:29]([C:30](N2C=CN=C2)=[O:31])=[CH:28][CH:27]=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][CH2:24][Br:25])=O)(C)(C)C.[OH-].[Na+].[NH2:41][CH2:42][CH:43]([OH:46])[CH2:44][OH:45]>C(Cl)(Cl)Cl>[Br:25][CH2:24][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:26]1[CH:27]=[CH:28][C:29]([C:30]([NH:41][CH2:42][CH:43]([OH:46])[CH2:44][OH:45])=[O:31])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 735613-Amino-1,2-propanediolHCID 20482510HCID 20482510, compound

Product 1

HCID 20554714HCID 20554714, 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-(16-bromohexadecyl)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 solid 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 solid is evaporated
  5. customThe solvent is again evaporated
  6. customthe oil is crystallized from acetone

Sources & evidence

ORD record
ord-a049995763f24ce6a9d35a9945505f8c
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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