tert-Butyl acetate → HCID 91478440, 화합물

HRID 1818632노트

반응식

HRID 1818632 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH3:12].[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]([C:36](OCC)=[O:37])=[CH:23]2>C1COCC1>[CH2:29]([N:25]1[C:26]2[C:22](=[CH:21][C:20]([Cl:19])=[CH:28][CH:27]=2)[CH:23]=[C:24]1[C:36](=[O:37])[CH2:12][C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

참가 물질

5

반응물 3

HCID 10908tert-Butyl acetateHCID 2733832Lithium HexamethyldisilazideHCID 13295699Ethyl 1-benzyl-5-chloroindole-2-carboxylate

생성물 1

HCID 91478440HCID 91478440, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cooled (−78° C.) solution of LHMDS (38 mL, 1.0 M in THF, 38 mmol) was added tert-butyl acetate (5.2 mL, 38.3 mmol). After 30 min, a solution of the title compound of Example 12 Step A (4.00 g, 12.8 mmol) in THF (10 mL) was added, and the mixture was held at −78° C. for 50 min, whereupon it was placed in a 0° C. bath. After 2 h, the reaction mixture was quenched by addition of sat. aq. NH4Cl, and the aqueous phase was extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 20%, then 20-100% EtOAc in hexanes) provided the title compound: LCMS B, tr=2.70 min, m/z 328.1 [M−tBu+H]+; 1H NMR (500 MHz, CDCl3) δ 7.70 (s, 1H), 7.31 (s, 1H), 7.29-7.18 (m, 5H), 7.02 (d, J=7.0 Hz, 2H), 5.84 (s, 2H), 3.86 (s, 2H), 1.40 (s, 9H).

후처리

  1. waitthe mixture was held at −78° C. for 50 min, whereupon it
  2. customwas placed in a 0° C.
  3. waitAfter 2 h
  4. customthe reaction mixture was quenched by addition of sat. aq. NH4Cl
  5. extractionthe aqueous phase was extracted with EtOAc
  6. dry with materialThe organic phase was dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel (0 to 20%

출처 및 근거

ORD 기록
ord-a2acdc97886144aabd15a941622e6f76
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598398B2

반응 노트

불러오는 중…