Sodium Hydroxide → HCID 20536453, compound

HRID 1156128Notes

Reaction equation

HRID 1156128 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]C(OC(C)(C)C)=O)[C:5](N1C=CN=C1)=[O:6].[OH-].[Na+].[NH2:41][CH2:42][CH:43]([OH:46])[CH2:44][OH:45]>C(Cl)(Cl)Cl>[OH:46][CH:43]([CH2:44][OH:45])[CH2:42][NH:41][C:5](=[O:6])[C:4]1[CH:12]=[CH:13][C:14]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 735613-Amino-1,2-propanediolHCID 54143056HCID 54143056, compound

Product 1

HCID 20536453HCID 20536453, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture containing 4.3 g. of 1-{3-fluoro-4-[N-(tert-butyloxycarbonyl)hexadecylamino]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 N-(2,3-dihydroxypropyl)-3-fluoro-4-(hexadecylamino)benzamide.

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-2f2deb93887044d8b201bf0dfaf4b1c4
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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