Hydrochloric Acid → HCID 178515745, compound
Reaction equation
O.Cl.[NH2:3][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:5][SH:6].[OH-].[Na+].[C:12]([C:14]1[S:15][C:16]2[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:17]=2[N:18]=1)#N.Cl>CO.O>[CH2:5]1[S:6]/[C:12](=[C:14]2/[N:18]=[C:17]3[C:16]([S:15]/2)=[CH:22][C:21](=[O:23])[CH:20]=[CH:19]3)/[NH:3][C@H:4]1[C:7]([OH:9])=[O:8]Participants
Procedure
685 mg. (3.9 mMol) D-cysteine hydrochloride monohydrate are dissolved in 13 ml. water which has been previously gassed with nitrogen. A pH value of 8 is adjusted, under an atmosphere of nitrogen, with about 6 ml. of a 1N aqueous sodium hydroxide solution and then a solution of 528 mg. (3 mMol) 2-cyano-6-hydroxybenzothiazole in 22 ml. methanol (analytically pure) is added thereto under an atmosphere of nitrogen. The yellow solution is stirred under an atmosphere of nitrogen and with the exclusion of light for 1 hour at ambient temperature. Subsequently, the solution is acidified with 3 ml. of 2N hydrochloric acid and left to stand for about 3 hours at 4° C. The precipitated crystals are filtered off with suction under an atmosphere of nitrogen, washed with methanol and water (1:1 v/v) and dried in a desiccator with the exclusion of light. 0.75 g. D-Luciferin are obtained, which corresponds to a yield of 89.3% of theory. The compound melts at 187°-188° C., with decomposition, and is chromatographically identical with the product known from the literature but contains small amounts of impurities.
Workup
- waitto stand for about 3 hours at 4° C
- filtrationThe precipitated crystals are filtered off with suction under an atmosphere of nitrogen
- washwashed with methanol and water (1:1 v/v)
- customdried in a desiccator with the exclusion of light
Sources & evidence
- ORD record
- ord-ebeaea12d238413dba497c4ea6e10a24
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04826989
Reaction notes
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