Hydrochloric Acid → HCID 178519975, 화합물

HRID 2169477노트

반응식

HRID 2169477 반응식
[Si]([O:8][CH2:9][CH2:10][N:11]([CH2:41][CH:42]1[CH2:44][CH2:43]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl>O1CCCC1>[CH:42]1([CH2:41][N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]3([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:15]=2)=[O:13])[CH2:44][CH2:43]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 178455250HCID 178455250, 화합물

생성물 1

HCID 178519975HCID 178519975, 화합물수율 75.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylicacid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amide (446) (200 mg, 0.325 mmol) of in tetrahydrofuran (10 mL) was added (1N) aqueous HCl (2 mL). The mixture was stirred for 1 h at room temperature. After completion of the reaction, volatiles were removed, the residue diluted with water (10 mL) and pH was adjusted to 8 using NaHCO3. The mixture was extracted with ethyl acetate (2×30 mL), and the organic part was dried and concentrated. The resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography using 50-60% ethyl acetate in hexane as gradient polarity mobile phase to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid cyclopropylmethyl-(2-hydroxyethyl)-amide (447) (123 mg, 75%) as a colorless gummy liquid.

후처리

  1. customAfter completion of the reaction, volatiles
  2. customwere removed
  3. additionthe residue diluted with water (10 mL) and pH
  4. extractionThe mixture was extracted with ethyl acetate (2×30 mL)
  5. customthe organic part was dried
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography

출처 및 근거

ORD 기록
ord-b41f40deaecd4ad3a9123eff218ca3cd
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

반응 노트

불러오는 중…