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tert-Butanol → [6-(5-tert-Butoxycarbonylamino-thiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester

HRID 1798287
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인쇄 미리보기

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HRID 1798287 반응식
[CH2:1]([O:3][C:4]([CH2:6][CH:7]1[O:11][B:10]([OH:12])[C:9]2[CH:13]=[C:14]([O:18][C:19]3[S:20][C:21](C(O)=O)=[CH:22][N:23]=3)[CH:15]=[C:16]([CH3:17])[C:8]1=2)=[O:5])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.C([N:46]([CH2:49]C)CC)C.[CH3:51][C:52]([OH:55])([CH3:54])[CH3:53]>>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][CH:7]1[O:11][B:10]([OH:12])[C:9]2[CH:13]=[C:14]([O:18][C:19]3[S:20][C:21]([NH:46][C:49]([O:55][C:52]([CH3:54])([CH3:53])[CH3:51])=[O:34])=[CH:22][N:23]=3)[CH:15]=[C:16]([CH3:17])[C:8]1=2)[CH3:2]
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참가 물질

5

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 582928242-(3-Ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-thiazole-5-carboxylic acid

생성물 1

HCID 58292561[6-(5-tert-Butoxycarbonylamino-thiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester
수율 45%

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온도
95 °C

실험 절차

To a solution of 2-(3-ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-thiazole-5-carboxylic acid (500 mg, 1.33 mmol) in tBuOH (10 mL) was added diphenylphosphoryl azide (0.35 mL, 1.61 mmol) and triethylamine (0.41 mL, 2.95 mmol), the reaction mixture was heated to 95° C. for 1 h. The solvent was removed under vacuum and the residue was extracted with ethyl acetate. The organic portion was washed with water and brine, and dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica, DCM/MeOH=20:1) affording the title compound (270 mg, 45%) as a white solid. 1H NMR (CDCl3) δ 7.35 (s, 1H), 7.10 (s, 1H), 6.79 (s, 1H), 5.61 (dd, 1H), 4.17 (q, 2H), 3.02 (dd, 1H), 2.37 (m, 1H), 2.30 (s, 3H), 1.48 (s, 9H), 1.23 (t, 3H).

후처리

  1. customThe solvent was removed under vacuum
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic portion was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica, DCM/MeOH=20:1)

출처 및 근거

ORD 기록
ord-4e60926bc7d4432da1bd4db90c91d0cb
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08343944B2

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