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Hydrochloric Acid → {[(3S,5R)-1-(tert-butoxycarbonyl)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl](2-methylpropyl)amino}(oxo)acetic acid

HRID 1184079
Notes
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Reaction equation

HRID 1184079 reaction equation
C([O:3][C:4](=[O:33])[C:5]([N:7]([CH2:29][CH:30]([CH3:32])[CH3:31])[C@H:8]1[CH2:13][C@@H:12]([C:14]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])[CH2:11][N:10]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:9]1)=[O:6])C.[OH-].[Na+].Cl>C(O)C>[C:25]([O:24][C:22]([N:10]1[CH2:11][C@H:12]([C:14]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[O:15])[CH2:13][C@H:8]([N:7]([C:5](=[O:6])[C:4]([OH:33])=[O:3])[CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:9]1)=[O:23])([CH3:27])([CH3:28])[CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58355657tert-butyl (3S,5R)-3-{[ethoxy(oxo)acetyl](2-methylpropyl)amino}-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

Product 1

HCID 58355189{[(3S,5R)-1-(tert-butoxycarbonyl)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl](2-methylpropyl)amino}(oxo)acetic acidYield 106.4%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

To a solution of tert-butyl (3S,5R)-3-{[ethoxy(oxo)acetyl](2-methylpropyl)amino}-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (10.3 g) in ethanol (40 ml) was added 2M aqueous sodium hydroxide solution (22 ml), and the mixture was stirred at room temperature for 6 hr. The reaction mixture was adjusted to pH 7 with 1M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (10.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9b6de261257d4e33aa6fdb4001d9496a
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08664380B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes