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Hydrochloric Acid → (2-Cyclopropylcarbamoyl-2-hydroxy-1,1-dimethylethyl)-carbamic acid tert-butyl ester

HRID 907649
Notes
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Reaction equation

HRID 907649 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:22])([CH3:21])[CH:10]([O:17]C(=O)C)[C:11](=[O:16])[NH:12][CH:13]1[CH2:15][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([CH3:22])([CH3:21])[CH:10]([C:11](=[O:16])[NH:12][CH:13]1[CH2:15][CH2:14]1)[OH:17])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67384759Acetic acid 2-tert-butoxycarbonylamino-1-cyclopropylcarbamoyl-2-methylpropyl ester

Product 1

HCID 67385732(2-Cyclopropylcarbamoyl-2-hydroxy-1,1-dimethylethyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acetic acid 2-tert-butoxycarbonylamino-1-cyclopropylcarbamoyl-2-methylpropyl ester in MeOH (10 mL) was added 10% NaOH (1.5 mL). The reaction mixture was stirred at room temperature for 3 h and then acidified with 1N Hydrochloric acid to pH 7. The reaction mixture was extracted with EtOAc. The organic layer was dried (Na2SO4) concentrated to yield (2-cyclopropylcarbamoyl-2-hydroxy-1,1-dimethylethyl)-carbamic acid tert-butyl ester which was used in the next step without further purification.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-79afd4ecbe5b4495a4ea50f3218583b1
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08013183B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes