Methyl 4-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-propyn-1-yl]benzoate → 847460-43-9

HRID 2221449Notes

Reaction equation

HRID 2221449 reaction equation
C([NH:8][CH2:9][C:10]#[C:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)(OC(C)(C)C)=O.[ClH:22].O1CCOCC1>C1COCC1>[ClH:22].[NH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 18617679Methyl 4-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-propyn-1-yl]benzoateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 69202155847460-43-9Yield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(N-Boc-3-aminoprop-1-ynyl)benzoate (3.40 g, 11.7 mmol) in THF (25 ml) was added 4M HCl/dioxane (25 ml, 100 mmol). The reaction mixture was stirred for 1 h. The formed precipitate was collected, washed with diethyl ether (200 ml) and dried in vacuo providing methyl 4-(3-aminoprop-1-ynyl)benzoate hydrochloride (2.46 g) as white solid. Alternatively, the N-Boc protected amine can be dissolved in methanol instead of THF. In this case the solvent was removed in vacuo and the precipitate was washed with diethyl ether.

Workup

  1. customThe formed precipitate was collected
  2. washwashed with diethyl ether (200 ml)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b3ba8de68e9f4f7f900eb048f39586b9
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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