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4-Acetylbenzoic Acid → 4-Acetyl-N-((5S)-5-amino-5-carbamoylpentyl)benzamide

HRID 2112421
Notes
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Reaction equation

HRID 2112421 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:25]([OH:27])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.O[N:36]1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.C(N(C(C)C)C(C)C)C.[C:63]([C:66]1[CH:74]=[CH:73][C:69]([C:70]([OH:72])=O)=[CH:68][CH:67]=1)(=[O:65])[CH3:64]>CN1CCCC1=O.ClCCl>[C:63]([C:66]1[CH:67]=[CH:68][C:69]([C:70]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]([NH2:1])[C:25](=[O:27])[NH2:36])=[O:72])=[CH:73][CH:74]=1)(=[O:65])[CH3:64]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 114704-Acetylbenzoic AcidHCID 12734Diisopropylcarbodiimide2×HCID 757711-Hydroxybenzotriazole2×HCID 81531Diisopropylethylamine2×HCID 10983524(2S)-2-(((tert-butoxy)carbonyl)amino)-6-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid

Product 1

HCID 11173833
4-Acetyl-N-((5S)-5-amino-5-carbamoylpentyl)benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent4×

Procedure

Rink-amide-resin (loading: 0.43 mmol/g, 6.66 g, 2.86 mmol) was swelled with dichloromethane (50 ml). The solvent was removed. A 20% solution of piperidine in N-methylpyrrolidinone was added (50 ml). The reactor was shaken for 20 min. The liquid was removed. The resin was washed with N-methylpyrrolidinone (3×50 ml) and dichloromethane (5×50 ml). A solution of BOC-Lys(FMOC)-OH (5.37 g, 11.5 mmol) in N-methylpyrrolidinone (50 ml) and a solution of 1-hydroxybenzotriazole (1.75 g, 11.5 mmol) in N-methylpyrrolidinone (20 ml) were added successively. Diisopropylcarbodiimide (1.79 ml, 11.5 mmol) and ethyldiisopropylamine (1.96 ml, 11.5 mmol) were added. The reactor was shaken at room temperature for 16 h. The liquid was removed. The resin was washed with N-methylpyrrolidinone (3×50 ml) and dichloromethane (3×50 ml). A solution of 4-acetylbenzoic acid (2.82 g, 11.5 mmol) in N-methylpyrrolidinone (50 ml) and a solution of 1-hydroxybenzotriazole (1.75 g, 11.5 mmol) in N-methylpyrrolidinone (20 ml) were added successively. Diisopropylcarbodiimide (1.79 ml, 11.5 mmol) and ethyldiisopropylamine (1.96 ml, 11.5 mmol) were added. The reactor was shaken at room temperature for 16 h. The resin was washed with N-methylpyrrolidinone (3×50 ml) and dichloromethane (3×50 ml). A solution of 50% of trifluoroacetic acid and 10% triisopropylsilane in dichloromethane (50 ml) was added to the resin. The reaction vessel was shaken for 1 h at room temperature. The liquid was collected. The solvent was removed in vacuo. The residue was redissolved in toluene (50 ml). The solvent was removed in vacuo.

Workup

  1. customThe solvent was removed
  2. additionA 20% solution of piperidine in N-methylpyrrolidinone was added (50 ml)
  3. customThe liquid was removed
  4. washThe resin was washed with N-methylpyrrolidinone (3×50 ml) and dichloromethane (5×50 ml)
  5. stirringThe reactor was shaken at room temperature for 16 h
  6. customThe liquid was removed
  7. washThe resin was washed with N-methylpyrrolidinone (3×50 ml) and dichloromethane (3×50 ml)
  8. stirringThe reactor was shaken at room temperature for 16 h
  9. washThe resin was washed with N-methylpyrrolidinone (3×50 ml) and dichloromethane (3×50 ml)
  10. additionA solution of 50% of trifluoroacetic acid and 10% triisopropylsilane in dichloromethane (50 ml) was added to the resin
  11. stirringThe reaction vessel was shaken for 1 h at room temperature
  12. customThe liquid was collected
  13. customThe solvent was removed in vacuo
  14. dissolutionThe residue was redissolved in toluene (50 ml)
  15. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e99beccf6ac04d058c359f6638e97efb
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07524813B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes