Sodium Hydroxide → HCID 20198306, compound

HRID 652036Notes

Reaction equation

HRID 652036 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][Si:36]([CH3:39])([CH3:38])[CH3:37])[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+].[NH2:42][CH2:43][CH:44]([OH:47])[CH2:45][OH:46]>C(Cl)(Cl)Cl>[OH:47][CH:44]([CH2:45][OH:46])[CH2:43][NH:42][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][Si:36]([CH3:37])([CH3:38])[CH3:39])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 735613-Amino-1,2-propanediolHCID 178453380HCID 178453380, compound

Product 1

HCID 20198306HCID 20198306, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture containing 4.2 g. of 1-[4-[N-(tert-butyloxycarbonyl)-4-[14-(trimethylsilyl)tetradecylamino]benzoyl)imidazole, 50 ml. of chloroform, and 50 ml. of 5N 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 1N 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 to yield the product as a light yellow solid.

Workup

  1. additionTo a mixture containing 4.2 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

Sources & evidence

ORD record
ord-995669c221904d868f0bd7921189af0b
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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