Hydrochloric Acid → 2-(2-Tritylamino-4-thiazolyl)-2-cyanomethoxyimino-acetic acid
Reaction equation
[OH-].[Na+].[C:3]([CH2:5][O:6][N:7]=[C:8]([C:15]1[N:16]=[C:17]([NH:20][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:18][CH:19]=1)[C:9]([O:11]CC#N)=[O:10])#[N:4].Cl>O1CCOCC1>[C:3]([CH2:5][O:6][N:7]=[C:8]([C:15]1[N:16]=[C:17]([NH:20][C:21]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:18][CH:19]=1)[C:9]([OH:11])=[O:10])#[N:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
17.1 ml of N sodium hydroxide solution was added dropwise over 20 minutes to a mixture of 8.69 g of the product of Step A in 52 ml of dioxane in an ice bath and the mixture was abandoned whereby there was a spontaneous heating. 10.5 ml of 2 N hydrochloric acid were added thereto and the dioxane and almost all the water was evaporated. 20 ml of water and 30 ml of ether were added thereto and the mixture was stirred for 15 minutes. The crystals were recovered by vacuum filtration, were rinsed with water and ether and dried to obtain 4.32 g of the syn isomer of 2-(cyanomethyloxyimino)-2-(2-tritylamino-4-thiazolyl)-acetic acid with a melting point of 180° C. (with decomposition).
Workup
- customthe dioxane and almost all the water was evaporated
- addition20 ml of water and 30 ml of ether were added
- filtrationThe crystals were recovered by vacuum filtration
- washwere rinsed with water and ether
- customdried
Sources & evidence
- ORD record
- ord-d1edff723d1c42a99a36fe7e15dc110f
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04439433
Reaction notes
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