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Hydrochloric Acid → 2-Benzyloxycarbonylamino-3-((3-methyl-4-oxo-1-phenyl-1,3,8,-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acid

HRID 896276
Notes
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Reaction equation

HRID 896276 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:5][NH:6][C:7]([N:9]1[CH2:26][CH2:25][C:12]2([N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][N:14]([CH3:23])[C:13]2=[O:24])[CH2:11][CH2:10]1)=[O:8].Cl>O1CCCC1.[OH-].[Li+]>[CH2:31]([O:30][C:28]([NH:27][CH:4]([CH2:5][NH:6][C:7]([N:9]1[CH2:26][CH2:25][C:12]2([N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][N:14]([CH3:23])[C:13]2=[O:24])[CH2:11][CH2:10]1)=[O:8])[C:3]([OH:38])=[O:2])=[O:29])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 208149142-Benzyloxycarbonylamino-3-((3-methyl-4-oxo-1-phenyl-1,3,8,-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acid methyl ester

Product 1

HCID 223500082-Benzyloxycarbonylamino-3-((3-methyl-4-oxo-1-phenyl-1,3,8,-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acidYield 83%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 177 mg (0.34 mmol) of 2-benzyloxycarbonylamino-3-((3-methyl-4-oxo-1-phenyl-1,3,8,-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acid methyl ester in 4 ml of tetrahydrofuran, 4 ml of 0.1M aqueous lithium hydroxide solution was added, and the resulting mixture was stirred overnight at 0° C. To the reaction mixture, 0.1M hydrochloric acid was added, and the resulting mixture was extracted with ethyl acetate. Organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated. The residue was reprecipitated from ether/chloroform to obtain 143 mg of 2-benzyloxycarbonylamino-3-((3-methyl-4-oxo-1-phenyl-1,3,8,-triazaspiro[4.5]decane-8-carbonyl)amino)propionic acid (yield: 83%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was reprecipitated from ether/chloroform

Sources & evidence

ORD record
ord-8d3314926f854874820660065181be03
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06919349B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes