Imidazole → 3-[(Tert-butyldimethylsilyloxy)methyl]-6-[methyloxy[3-hydroxyquinoxalin-2-yl]]-1,2-dithiin

HRID 265316

반응식

HRID 265316 반응식
O[CH2:2][C:3]1[S:4][S:5][C:6]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:7][CH:8]=1.[Si](OC1[C:27]([OH:36])=[N:28][C:29]2[C:34]([N:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2)(C(C)(C)C)(C)C.[OH:37][C:38]1C(O)=NC2C(=CC=CC=2)N=1.[Si](Cl)(C(C)(C)C)(C)C.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Si:11]([O:10][CH2:9][C:6]1[S:5][S:4][C:3]([C:2]2[C:27]([OH:36])=[N:28][C:29]3[C:34](=[CH:33][CH:32]=[CH:31][C:30]=3[O:37][CH3:38])[N:35]=2)=[CH:8][CH:7]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

참가 물질

9

반응물 7

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 28928tert-Butyldimethylsilyl chlorideHCID 5462977Diethyl azodicarboxylateHCID 100628323-[(Tert-butyldimethylsilyloxy)methyl]-6-hydroxymethyl-1,2-dithiinHCID 1784551103-(Tert-butyldimethylsilyloxy)-2-hydroxyquinoxalineHCID 178517140HCID 178517140, 화합물

생성물 1

HCID 1784889283-[(Tert-butyldimethylsilyloxy)methyl]-6-[methyloxy[3-hydroxyquinoxalin-2-yl]]-1,2-dithiin수율 28.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 3-(hydroxymethyl)-6-[(tert-butyldimethylsilyloxy)methyl]-1,2-dithiin (U.S. Ser. No. 08/212,096) (200 mg, 0.688 mmol) of in 2 mL dry THF was added a solution of 3-(tert-butyldimethylsilyloxy)-2-hydroxyquinoxaline obtained from the reaction of 2,3-dihydroxyquinoxaline with tert-butyldimethylsilyl chloride and imidazole as in Example 6 (248 mg, 1.753 mmol) in 2 mL THF, followed by addition of triphenylphosphine (220 mg, 0.839 mmol). The resulting solution was cooled to 0° C., then 140 μL (155 mg, 0.890 mmol) of diethylazodicarboxylate was added, and the reaction mixture was kept at 0°-5° C. for 2 h until TLC analysis showed the reaction to be complete. For isolation of the products, the reaction mixture poured directly onto a silica gel column and eluted with ethyl acetate-hexane, 1:6, to give 3-[(tert-butyldimethylsilyloxy)methyl]-6-[methyloxy[3-hydroxyquinoxalin-2-yl]]-1,2-dithiin (104 mg, 28.2%). No product of N-alkylation was isolated; MS (+LSIMS) 549.4 (MH+).

후처리

  1. customthe reaction
  2. additionFor isolation of the products, the reaction mixture poured directly onto a silica gel column
  3. washeluted with ethyl acetate-hexane, 1:6

출처 및 근거

ORD 기록
ord-7f775397e4964fcb85517dbb0ba849bd
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648354

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