1,2-Dichloroethane → (2S,2S)-nicotinic acid 2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-(2-methoxycarbonylamino-3,3-diphenyl-propionylamino)-hexyl ester

HRID 132703

반응식

HRID 132703 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:17]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:7][O:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:53][O:54][C:55]([NH:57][C@@H:58]([CH:62]([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:59](O)=[O:60])=[O:56]>CN(C=O)C>[NH2:31][C:28]1[CH:27]=[CH:26][C:25]([S:22]([N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C@@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:59](=[O:60])[C@@H:58]([NH:57][C:55]([O:54][CH3:53])=[O:56])[CH:62]([C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH2:7][O:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=2)(=[O:24])=[O:23])=[CH:30][CH:29]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acidHCID 131726927(2S)-nicotinic acid 6-amino-2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-hexyl ester

생성물 1

HCID 11721810(2S,2S)-nicotinic acid 2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-(2-methoxycarbonylamino-3,3-diphenyl-propionylamino)-hexyl ester수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The product of step B, (2S)-nicotinic acid 6-amino-2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-hexyl ester (100 mg, 0.22 mmol) was dissolved in anhydrous DMF (2 mL) and treated with 0.062 mL (0.45 mmol) of triethylamine followed by EDC (100 mg, 0.56 mmol), HOBt (75 mg, 0.56 mmol) and (2S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid (56 mg, 0.19 mmol). The mixture was stirred overnight at room temperature. The product was extracted with ethyl acetate (40 mL) and water (40 mL). The organic layer was separated and dried with Na2SO4, then evaporated to give 160 mg of crude oil. The residue was purified by flash chromatography with a mixture of eluents hexane/ethyl acetate (2/8). The title compound was obtained as a clear oil in 20% yield (25 mg).

후처리

  1. extractionThe product was extracted with ethyl acetate (40 mL) and water (40 mL)
  2. customThe organic layer was separated
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customto give 160 mg of crude oil
  6. customThe residue was purified by flash chromatography with a mixture of eluents hexane/ethyl acetate (2/8)

출처 및 근거

ORD 기록
ord-243b3a79396548279078ae79ee734d05
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388008B2

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