Methanol → (4-Amino-butyl)-(4-tert-butoxycarbonylamino-butyl)-carbamic acid tert-butyl ester

HRID 1503086노트

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HRID 1503086 반응식
C1C(C(NCCCNCCCCNC(C[C:22](O)([C:46](O)=O)[CH2:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31]CCCNC(C2C=CC(O)=C(O)C=2)=O)=O)=O)=O)=CC(O)=C(O)C=1.[C:52]([O-:55])([O-:54])=O.[K+].[K+].C1(C(Cl)=O)[CH:63]=[C:62]([C:64](Cl)=O)[CH:61]=C(C(Cl)=O)C=1.[NH4+:73].[OH-:74].[CH3:75][OH:76]>C(Cl)Cl.O>[C:62]([O:74][C:75](=[O:76])[N:26]([CH2:24][CH2:23][CH2:22][CH2:46][NH2:73])[CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:52]([O:55][C:62]([CH3:61])([CH3:63])[CH3:64])=[O:54])([CH3:64])([CH3:63])[CH3:61]

참가 물질

8

반응물 5

HCID 887MethanolHCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 78138Trimesoyl chlorideHCID 11411510Petrobactin

생성물 1

HCID 86761292(4-Amino-butyl)-(4-tert-butoxycarbonylamino-butyl)-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

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온도
0 °C

실험 절차

A solution of (4-Amino-butyl)-(4-tert-butoxycarbonylamino-butyl)-carbamic acid tert-butyl ester 12 (460 mg, 1.28 mmol) and CH2Cl2 (3 mL) was prepared. Note: 12 is a known compound (ref: “Total Synthesis of Petrobactin and Its Homologues as Potential Growth Stimuli for Marinobacter hydrocarbonoclasticus, an oil-degrading bacteria.” Gardner, R. A.; Kinkade, R.+; Wang, C.; Phanstiel IV, O. J. Org. Chem. 2004, 69, 3530-3537). A solution of K2CO3 (420 mg, 3.04 mmol) and water (5 mL) was added to the original mixture. Aliquat (0.10 mL) was added and the mixture was cooled to 0° C. 1,3,5-benzenetricarboxylic acid chloride 11 (105 mg, 0.395 mmol) in CH2Cl2 (6 mL) was added dropwise to the original mixture and allowed to gradually warm and stir vigorously at rt for 6 hours. TLC (95% CH2Cl2, 4% MeOH, 1% NH4OH Rf=0.35) was used to monitor the reaction. After the reaction was complete, the aqueous layer was extracted three times in CH2Cl2 and saturated Na2CO3. The organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated to give 590 mg of crude product. The crude was subjected to flash column chromatography (95% CH2Cl2, 4% MeOH, 1% NH4OH Rf=0.35) to give 13 (382 mg, 0.310 mmol, 78%). 1H NMR (CDCl3): δ 8.41 (s, 3H), 4.75 (br s, 3H), 3.49 (m, 6H), 3.23-3.06 (m, 18H), 2.78-1.30 (m, 78H).

후처리

  1. additionAliquat (0.10 mL) was added
  2. temperatureto gradually warm
  3. customthe reaction
  4. extractionthe aqueous layer was extracted three times in CH2Cl2
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 590 mg of crude product

출처 및 근거

ORD 기록
ord-dd447c3b8d694f819ee53f05e94b241c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212131B2

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