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Hydrochloric Acid → 2-(1-Benzyloxycarbonylamino-cyclopropyl)-oxazole-4-carboxylic acid

HRID 1040494
Notes
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Reaction equation

HRID 1040494 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2([NH:14][C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:13][CH2:12]2)[O:9][CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>C1COCC1>[CH2:18]([O:17][C:15]([NH:14][C:11]1([C:8]2[O:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[CH2:13][CH2:12]1)=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 584312412-(1-Benzyloxycarbonylamino-cyclopropyl)-oxazole-4-carboxylic acid ethyl ester

Product 1

HCID 584311512-(1-Benzyloxycarbonylamino-cyclopropyl)-oxazole-4-carboxylic acidYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
70 °C

Procedure

2-(1-Benzyloxycarbonylamino-cyclopropyl)-oxazole-4-carboxylic acid ethyl ester (0.44 g, 1.3 mmol) was dissolved in THF (10 mL) and to this solution was added 2N NaOH (2.0 mL, 4.0 mmol). The mixture was heated at 70° C. for 17 h. The mixture was neutralized with 2N HCl and extracted with EtOAc (3×100 mL). The combined extracts were washed with water, brine and dried with MgSO4. The mixture was filtered and concentrated to give 2-(1-benzyloxycarbonylamino-cyclopropyl)-oxazole-4-carboxylic acid (0.22 g, 0.73 mmol) as a brown solid.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined extracts were washed with water, brine
  3. dry with materialdried with MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-04a4e398641d48a3a3290a1dbe6c88f4
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552205B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes