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Hydrochloric Acid → HCID 9932381, compound

HRID 651342
Notes
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Reaction equation

HRID 651342 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][N:5]1[C:9](=[O:10])[C:8]2([CH2:15][CH2:14][N:13]([CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[N:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:6]1.[OH-].[Na+].ClCCl.Cl>C(O)C>[C:17]1([CH2:16][N:13]2[CH2:14][CH2:15][C:8]3([N:7]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:6][N:5]([CH2:4][C:3]([OH:33])=[O:2])[C:9]3=[O:10])[CH2:11][CH2:12]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 98034758-(1-Naphthalenylmethyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-3-acetic acid Methyl Ester

Product 1

HCID 9932381HCID 9932381, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

(8-Naphthalen-1-ylmethyl-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-3-yl)-acetic acid methyl ester (44.40 g, 0.1 mol, prepared as described above) was dissolved in a mixture of 2 N sodium hydroxide (165 ml, 0.33 mol) and ethanol (500 ml) and stirred at room temperature for 16 h. Dichloromethane (700 ml) was added and pH was adjusted to 5 by the addition of 6 N hydrochloric acid. The organic phase was separated, washed with water (2×200 ml and concentrated to 300 ml in vacuo. Water (300 ml) and dichloromethane (100 ml) were added and the slurry was stirred overnight. The product was collected by filtration, washed successively with water (4×100 ml, dichloromethane (2×50 ml) and acetone (2×50 ml) and dried, affording the title compound as a powder (44.6 g, 97% yield).

Workup

  1. customThe organic phase was separated
  2. washwashed with water (2×200 ml
  3. concentrationconcentrated to 300 ml in vacuo
  4. additionWater (300 ml) and dichloromethane (100 ml) were added
  5. stirringthe slurry was stirred overnight
  6. filtrationThe product was collected by filtration
  7. washwashed successively with water (4×100 ml, dichloromethane (2×50 ml) and acetone (2×50 ml)
  8. customdried

Sources & evidence

ORD record
ord-ddebb3758d9f4d178442cc9d09706a6c
Source dataset
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06277991B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes