Hydrochloric Acid → HCID 178515811, 화합물

HRID 1173830노트

반응식

HRID 1173830 반응식
C([Si](C)(C)[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:9][CH2:8]1)(C)(C)C.[Li+].CC([N-]C(C)C)C.Br[CH2:30][C:31]1[S:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[C:32]=1[Cl:40].Cl>CO.O.C1COCC1>[Cl:40][C:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[S:35][C:31]=1[CH2:30][CH:15]1[CH2:16][CH2:17][N:13]([C@H:10]2[CH2:9][CH2:8][C@@H:7]([OH:6])[CH2:12][CH2:11]2)[C:14]1=[O:18]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8167082-(Bromomethyl)-3-chloro-1-benzothiopheneHCID 2724682Lithium diisopropylamideHCID 178455336HCID 178455336, 화합물

생성물 1

HCID 178515811HCID 178515811, 화합물수율 71%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Charge a flask with cis-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (0.50 g, 1.68 mmol) (1.0 eq), dissolve with THF (0.2 M) and cool to −78° C. Add LDA (1.1 to 1.5 eq) and stir at −78° C. for 5 minutes. Add 2-bromomethyl-3-chloro-benzo[b]thiophene (U.S. Pat. No. 4,939,140) (0.53 g, 2.02 mmol) and warm to room temperature overnight. Dilute with methanol (0.2 M) and add concentrated HCl (10 eq.) and stir at room temperature. Pour into water after reaction complete by HPLC and extract with methylene chloride, dry over sodium sulfate, filter and concentrate in vacuo. Purification of the residue over silica gel (20% hexane in ethyl acetate) affords the title compound as a white powder (0.44 g, 71%): MS (APCI-pos mode) m/z (rel intensity) 364.1 (100), 366.1 (40).

후처리

  1. temperature4,939,140) (0.53 g, 2.02 mmol) and warm to room temperature overnight
  2. customafter reaction complete by HPLC
  3. extractionextract with methylene chloride
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurification of the residue over silica gel (20% hexane in ethyl acetate)

출처 및 근거

ORD 기록
ord-2becacd583fc4e6b955360d28d37b702
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834194B2

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