Hydrochloric Acid → tert-Butyl 3-(3-(2H-tetrazol-5-yl)phenethoxy)propanoate

HRID 909900노트

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HRID 909900 반응식
Cl.C(N(CC)CC)C.[C:9]([C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][O:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])#[N:10].[N-:29]=[N+:30]=[N-:31].[Na+].Cl>O.C(O)(C)(C)C>[N:10]1[NH:29][N:30]=[N:31][C:9]=1[C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][O:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 58168561tert-Butyl 3-(3-cyanophenethoxy)propanoate

생성물 1

HCID 67076178tert-Butyl 3-(3-(2H-tetrazol-5-yl)phenethoxy)propanoate

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

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온도
140 °C

실험 절차

Triethylamine hydrochloride (2.09 g) was added in one portion to a mixture of tert-butyl 3-(3-cyanophenethoxy)propanoate [Example 7, Step i)] (1.74 g), sodium azide (0.99 g) and tert-butanol (12.64 mL), and sealed into a microwave tube. The reaction was heated to 140° C., over a period of 2 h in the microwave reactor. The reaction mixture was diluted with water and acidified with 2M hydrochloric acid (5 mL). The mixture was extracted with DCM and the organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 20-100% ethyl acetate in isohexane, then elution gradient 0-10% methanol in DCM to afford the subtitled compound (1.77 g). 1H NMR (300 MHz, CDCl3) δ 8.11 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 7.44 (t, J=7.7 Hz, 1H), 7.31 (d, J=7.7 Hz, 1H), 3.79 (t, J=5.3 Hz, 2H), 3.75 (t, J=5.6 Hz, 2H), 2.96 (t, J=5.2 Hz, 2H), 2.63 (t, J=5.3 Hz, 2H), 1.48 (s, 9H).

후처리

  1. customsealed into a microwave tube
  2. extractionThe mixture was extracted with DCM
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product
  7. customThe crude product was purified by flash silica chromatography, elution gradient 20-100% ethyl acetate in isohexane
  8. washelution gradient 0-10% methanol in DCM

출처 및 근거

ORD 기록
ord-e6eee0472922456388452656839ab281
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017602B2

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