Sodium Hydroxide → HCID 20331329, compound

HRID 2057673Notes

Reaction equation

C(OC([C:8]1([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]#[C:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[CH:20]=[CH:19][C:11]([C:12](N2C=CN=C2)=[O:13])=[CH:10][CH2:9]1)=O)(C)(C)C.[OH-].[Na+].[NH2:44][CH2:45][CH:46]([OH:49])[CH2:47][OH:48]>C(Cl)(Cl)Cl>[OH:49][CH:46]([CH2:47][OH:48])[CH2:45][NH:44][C:12](=[O:13])[C:11]1[CH:10]=[CH:9][C:8]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]#[C:34][C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture containing 4.3 g. of 1-{4-(tert-butyloxycarbonyl)-4-[13-(4-chlorophenyl)tridec-12-ynylamino]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 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)-4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzamide.

Workup

additionTo a mixture containing 4.3 g
customthe layers are separated
washthe chloroform solution is washed once with 50 ml
customThe solvent is evaporated
customThe solvent is again evaporated
customthe oil is crystallized from acetone

Sources & evidence

ORD record: ord-9394948bd17f49f780fc0661fc274f7d
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04211783

Reaction notes

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