Diethyl Ether → HCID 18602836, compound
Reaction equation
[CH2:1]([O:8][C:9](=[O:40])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:39])[CH2:16][N:17]([C:27](=[O:38])[C@H:28]([CH3:37])[NH:29]C(OC(C)(C)C)=O)[CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)C.O1CCOCC1.[ClH:52]>>[ClH:52].[CH2:1]([O:8][C:9](=[O:40])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:39])[CH2:16][N:17]([C:27](=[O:38])[C@H:28]([CH3:37])[NH2:29])[CH:18]1[CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
N-t-butyloxycarbonyl-L-alanyl-N-(2-indanyl)glycyl-L-proline benzylester (2.72 g, 4.95 m mole) was dissolved in 4N hydrogen chloride dioxane solution (50 ml) and the mixture was stirred for 1 hour at room temperature. The solvent was distilled under reduced pressure from the solution, and thereby a sticky residue was obtained. After addition of ethyl ether the solution was filtered and a crystalline residue was obtained on the filter paper, and immediately dried in a desiccator to obtain a white powder of L-alanyl-N-(2-indanyl)glycyl-L-proline benzylester hydrochloride (2.31 g, 4.76 m mole, yield: 96%). This product had a hygrospic nature, and gave a single spot with Rf =0.42 by silica gel thin layer chromatography (developing solvent, chloroform:methanol:triethylamine=40:2:1, Colour forming method: spraying of 0.1% ninhydrin and heating).
Workup
- distillationThe solvent was distilled under reduced pressure from the solution
- customa sticky residue was obtained
- filtrationwas filtered
- customa crystalline residue was obtained on the filter paper
- customimmediately dried in a desiccator
Sources & evidence
- ORD record
- ord-29ba8cd6ecde4a24b0befdc8d7872b24
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04590178
Reaction notes
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