Hydrochloric Acid → Methyl 1-{[(3S)-3-amino-3-phenylpropyl]amino}cyclopentanecarboxylate bis-hydrochloride

HRID 1864896Notes

Reaction equation

HRID 1864896 reaction equation
C(OC([NH:8][C@H:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:10][CH2:11][NH:12][C:13]1([C:18]([O:20][CH3:21])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1)=O)(C)(C)C.[ClH:28]>CO>[ClH:28].[ClH:28].[NH2:8][C@H:9]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:10][CH2:11][NH:12][C:13]1([C:18]([O:20][CH3:21])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66973463Methyl 1-({(3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}amino)cyclopentanecarboxylate

Product 1

HCID 66973378Methyl 1-{[(3S)-3-amino-3-phenylpropyl]amino}cyclopentanecarboxylate bis-hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a cooled (0° C.) solution of methyl 1-({(3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}amino)cyclopentanecarboxylate from Step C (0.920 g, 2.44 mmol) in MeOH (49 mL) was added excess anhydrous hydrogen chloride gas. After 30 min the solution was purged with dry nitrogen for about 40 min. The solvent was then removed in vacuo to provide a solid/oil mix. Additional MeOH (50 mL) was then added and subsequently removed in vacuo to provide the title compound. MS: nm/z=277 (M+1).

Workup

  1. customAfter 30 min the solution was purged with dry nitrogen for about 40 min
  2. customThe solvent was then removed in vacuo
  3. customto provide a solid/oil
  4. additionmix
  5. customsubsequently removed in vacuo

Sources & evidence

ORD record
ord-c5700c132ff246da8b6bfdd478eb8b89
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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