Triphenylphosphine → HCID 178431455, 화합물

HRID 433035

반응식

HRID 433035 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[CH3:37])[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.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[Cl:89][C:90]1[CH:95]=[C:94]([Cl:96])[CH:93]=[CH:92][C:91]=1[CH2:97][CH2:98]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN(C=O)C.C1COCC1>[C:24]([C@@H:2]([NH:1][C:31](=[O:33])[C:30]1[CH:34]=[C:35]([OH:38])[C:36]([CH3:37])=[C:28]([O:27][CH2:98][CH2:97][C:91]2[CH:92]=[CH:93][C:94]([Cl:96])=[CH:95][C:90]=2[Cl:89])[CH:29]=1)[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:8])=[NH:23])(=[O:26])[NH2:41]

참가 물질

11

반응물 8

HCID 11776TriphenylphosphineHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 27340992,4-Dichlorophenethyl alcoholHCID 27480453,5-Dihydroxy-4-methylbenzoic AcidHCID 5363146Diisopropyl azodicarboxylateHCID 11708267BistrimethylsilylacetamidHCID 178454311HCID 178454311, 화합물

생성물 1

HCID 178431455HCID 178431455, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Rink resin (239 mg; loading 0.43 mmol/g) functionalized with Arg(Boc)2 was coupled with 106 mg of 3,5-dihydroxy-4-methylbenzoic acid in the presence of DIC (85 mg) and HOBt (90 mg) in DMF (1.5 ml). The resin was then washed and treated with a 15% solution of benzyltrimethylammonium hydroxide in DMF for 45 min. The resin was washed with DMF, 10% acetic acid in DMF, DMF and DCM and dried in vacuo for 4 h. The dried resin was washed with anhydrous THF and mixed with 145 mg (0.5 mmole) of triphenylphosphane and 25 μl of bistrimethylsilylacetamide in THF and kept at room temperature for 1 h. In a separate vial a mixture of 100 mg (0.2 mmol) of 2-(2,4-dichlorophenyl)ethanol and 100 μl of DIAD in dry THF was prepared. The reaction mixture was added to the resin which had previously been cooled in a refrigerator for 10 min. Coupling was continued at room temperature overnight. 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 15% solution of benzyltrimethylammonium hydroxide in DMF for 45 min
  3. washThe resin was washed with DMF, 10% acetic acid in DMF, DMF and DCM
  4. customdried in vacuo for 4 h
  5. washThe dried resin was washed with anhydrous THF
  6. customwas prepared
  7. additionThe reaction mixture was added to the resin which
  8. temperaturehad previously been cooled in a refrigerator for 10 min
  9. waitCoupling was continued at room temperature overnight
  10. washThe resin was washed
  11. customdried

출처 및 근거

ORD 기록
ord-011e9b4aaf294179b893e189ce80bcdf
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664393B2

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