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Tetrahydrofuran → tert-butyl N-[3-(4-methylpiperazin-1-yl)benzoyl]glycinate

HRID 2222578
Notes
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Reaction equation

HRID 2222578 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=O)[CH2:4][CH2:3]1.[C:17](Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH2:30][C@H:31]([C:36]([O-:38])=[O:37])C(C)(C)C.[CH2:39]1[CH2:43]OC[CH2:40]1>ClCCl.CN(C=O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([NH:30][CH2:31][C:36]([O:38][C:39]([CH3:40])([CH3:43])[CH3:17])=[O:37])=[O:13])[CH2:6][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 47416813-(4-Methylpiperazin-1-yl)benzoic acidHCID 77068310tert-Butylglycinate

Product 1

HCID 69161819tert-butyl N-[3-(4-methylpiperazin-1-yl)benzoyl]glycinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 3-(4-methylpiperazin-1-yl)benzoic acid (0.58 g, 2 mmol) in dichloromethane (50 mL) and DMF (2 drops), oxalyl chloride (0.9 mL, 10 mmol) was added dropwise at RT. After addition the reaction mixture was heated at 60° C. for 2 h. After concentration and stripping with toluene the crude acyl chloride was dissolved in dry THF (7 mL)/triethylamine (3 mmol) and t-butylglycinate (0.286 mL, 2.1 mmol) was added at RT and the reaction mixture was stirred at RT overnight. After concentration obtained 0.66 g (2 mmol, quant.) of tert-butyl N-[3-(4-methylpiperazin-1-yl)benzoyl]glycinate. The above obtained t-butyl ester (0.1 g, 0.3 mmol) was stirred at RT in dichloromethane (4 mL) and trifluoroacetic acid (3 mL) overnight. The solvents were removed under reduced pressure and the crude material stripped three times with toluene. Obtained the corresponding acid (0.080 g. 96% yield).

Workup

  1. additionwas added dropwise at RT
  2. additionAfter addition the reaction mixture
  3. concentrationAfter concentration
  4. additionwas added at RT
  5. concentrationAfter concentration

Sources & evidence

ORD record
ord-2b1ad052a7c54d3fb23a1a6287659fd2
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07371862B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes