HCID 18342923, compound → HCID 86625770, compound

HRID 2378004Notes

Reaction equation

HRID 2378004 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH:10]([C:24](=[O:29])[N:25]([O:27][CH3:28])[CH3:26])[CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[CH2:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[C:24](=[O:29])[N:25]([O:27][CH3:28])[CH3:26])=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 18342923HCID 18342923, compound

Product 1

HCID 86625770HCID 86625770, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of (RS)-2-(methoxy-methyl-carbamoyl)-piperazine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester (WO 01/00214) (5 g, 0.012 mol) in dichloromethane (100 ml) and trifluoroacetic acid (20 ml) was heated at 40° C. for 0.5 h, cooled and evaporated. The residual oil was dissolved in dichloromethane (150 ml) and washed with 1M sodium hydroxide (80 ml). The aqueous phase was re-extracted with dichloromethane (2×) and the combined extracts dried (Na2SO4) and the solvent removed in vacuo to give the title compound as an oil (3.6 g, 100%).

Workup

  1. temperaturecooled
  2. customevaporated
  3. dissolutionThe residual oil was dissolved in dichloromethane (150 ml)
  4. washwashed with 1M sodium hydroxide (80 ml)
  5. extractionThe aqueous phase was re-extracted with dichloromethane (2×)
  6. dry with materialthe combined extracts dried (Na2SO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-463ca2166d2d40ad8ea8376a062f77cd
Source dataset
uspto-grants-2008_12
Patent number
US07470710B2

Reaction notes

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