Triphenylphosphine → HCID 178512850, 화합물

HRID 433034

반응식

HRID 433034 반응식
[NH2:1][C@H:2]([C:24]([OH:26])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:23])[N:8](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.[OH:27][C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([OH:38])[C:36]=1[Br:37])[C:31]([OH:33])=O.CC(C)[N:41]=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:77][C:78]1[CH:83]=[C:82]([Cl:84])[CH:81]=[CH:80][C:79]=1[CH2:85][CH2:86]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN(C=O)C.C1COCC1>[Br:37][C:36]1[C:35]([OH:38])=[CH:34][C:30]([C:31]([NH:1][C@H:2]([C:24](=[O:26])[NH2:41])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:8])=[NH:23])=[O:33])=[CH:29][C:28]=1[O:27][CH2:86][CH2:85][C:79]1[CH:80]=[CH:81][C:82]([Cl:84])=[CH:83][C:78]=1[Cl:77]

참가 물질

10

반응물 7

HCID 11776TriphenylphosphineHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 860234-Bromo-3,5-dihydroxybenzoic acidHCID 27340992,4-Dichlorophenethyl alcoholHCID 5363146Diisopropyl azodicarboxylateHCID 178454311HCID 178454311, 화합물

생성물 1

HCID 178512850HCID 178512850, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Rink resin (500 mg; loading 0.3 mmol/g) functionalized with Arg(Boc)2 was coupled with 176 mg of 3,5-dihydroxy-4-bromobenzoic acid in the presence of DIC (110 mg) and HOBt (78 mg) in DMF. The resin was then washed and treated with a 30% solution of benzyltrimethylammonium hydroxide in DMF for 1 h. The resin was washed with DMF, 10% acetic acid in DMF, DMF, and DCM and dried in vacuo for 3 h. The dried resin was washed with anhydrous THF and mixed with 0.2 mmol of triphenylphosphane and 0.2 mmol of 2-(2,4-dichlorophenyl)ethanol in 2 ml of dry THF. The suspension of the resin was cooled in a refrigerator for 16 min and 50 μl (0.2 mmol) of DIAD in 0.5 ml of dry THF were added. Coupling was continued overnight at room temperature. The resin was washed with dry THF and the coupling was repeated for additional 8 h. The resin was washed and dried, and the final product was cleaved off and processed as described in Example 1.

후처리

  1. washThe resin was then washed
  2. additiontreated with a 30% solution of benzyltrimethylammonium hydroxide in DMF for 1 h
  3. washThe resin was washed with DMF, 10% acetic acid in DMF, DMF, and DCM
  4. customdried in vacuo for 3 h
  5. washThe dried resin was washed with anhydrous THF
  6. additionThe suspension of the resin
  7. temperaturewas cooled in a refrigerator for 16 min
  8. washThe resin was washed with dry THF
  9. waitthe coupling was repeated for additional 8 h
  10. washThe resin was washed
  11. customdried

출처 및 근거

ORD 기록
ord-6b819f116e134274b935d0f22d796e7d
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664393B2

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