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

HRID 2112421
ノート
印刷プレビュー

反応式

HRID 2112421 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒4 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e99beccf6ac04d058c359f6638e97efb
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07524813B2

反応ノート

読み込み中…

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