Ammonium Chloride → tert-Butyl 4-[4-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

HRID 2199174노트

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HRID 2199174 반응식
[CH:1]1([CH2:7][Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CON(C)[C:13]([C:15]1[N:16]=[C:17]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[S:18][CH:19]=1)=[O:14].[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH:1]1([CH2:7][C:13]([C:15]2[N:16]=[C:17]([CH:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]3)[S:18][CH:19]=2)=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 86660504tert-Butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylateHCID 178478994HCID 178478994, 화합물

생성물 1

HCID 67468980tert-Butyl 4-[4-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

Under argon and at −78° C., cyclohexylmethylmagnesium chloride 0.5M in diethyl ether (2.7 ml) was added dropwise to a solution of tert-butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (480 mg) in tetrahydrofuran (5 ml). The reaction mixture was stirred at −78° C. for one hour. The reaction mixture was then stirred at room temperature for one hour. Saturated ammonium chloride solution was then added to the reaction mixture, and the aqueous phase was separated off. After extraction of the aqueous phase with ethyl acetate, the combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. This gave tert-butyl 4-[4-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (335 mg).

후처리

  1. stirringThe reaction mixture was then stirred at room temperature for one hour
  2. customthe aqueous phase was separated off
  3. extractionAfter extraction of the aqueous phase with ethyl acetate
  4. dry with materialthe combined organic phases were dried over sodium sulphate
  5. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-263ff533434f4b51bb74d41ff2e49cb2
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09357779B2

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