Hydrochloric Acid → 1-[(4-{[(Tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]cyclobutanecarboxylic acid

HRID 16599Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:21]([O:23]CC)=[O:22])[CH2:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CCO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2([C:21]([OH:23])=[O:22])[CH2:18][CH2:19][CH2:20]2)[CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of Ethyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]cyclobutanecarboxylate (4.2 g, 11.9 mmol, Step 5), 2N NaOH (18 mL) and EtOH (12 mL) was heated at 50° C. for 4 hrs. The resulting solution was cooled in ice bath and 2N HCl (ca 19 mL) was added until pH of the mixture was ca 5-6. The whole was extracted with CH2Cl2/iPrOH (3:1, 30 mL×3). Combined organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated to give 3.8 g (98%) of the titled compound as yellow solid.

Workup

temperatureThe resulting solution was cooled in ice bath
extractionThe whole was extracted with CH2Cl2/iPrOH (3:1, 30 mL×3)
dry with materialCombined organic layer was dried (Na2SO4)
filtrationfiltered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-37338e18d41645afba9eb5b5f6a39cbd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737163B2

Reaction notes

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