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Sodium Chloride → Tert-butyl 4-(3-(5-bromo-2-(methoxycarbonyl)thiophen-3-yl)ureido)piperidine-1-carboxylate

HRID 1476618
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HRID 1476618 반응식
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:18]=[C:17]([Br:19])[S:16][C:15]=1[C:20]([O:22][CH3:23])=[O:21].[NH2:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1.[Cl-].[Na+]>C1COCC1.O>[Br:19][C:17]1[S:16][C:15]([C:20]([O:22][CH3:23])=[O:21])=[C:14]([NH:13][C:2]([NH:24][CH:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]2)=[O:4])[CH:18]=1
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참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 94429TriphosgeneHCID 12682914-Amino-1-Boc-piperidineHCID 20158931Methyl 3-amino-5-bromothiophene-2-carboxylate

생성물 1

HCID 67258128Tert-butyl 4-(3-(5-bromo-2-(methoxycarbonyl)thiophen-3-yl)ureido)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

Triphosgene (8.22 g) is dissolved in dry THF (345 ml) under argon atmosphere. The solution is cooled to 0° C. and a solution of methyl 3-amino-5-bromothiophene-2-carboxylate (19.8 g) in dry THF (173 ml) is added dropwise keeping the temperature below 10° C. The mixture is stirred for 14 h at RT. The reaction mixture is cooled to 0° C. again and a solution of tert-butyl 4-aminopiperidine-1-carboxylate (17.0 g) in dry THF (173 ml) is added within 15 min keeping the temperature below 10° C. After 15 min at 0° C. and additional 3 h at RT water (495 ml) and saturated aqueous sodium chloride solution (124 ml) are added. The organic layer is separated and the aqueous layer is extracted with THF three times (124 ml each). The combined organic layers are washed with half concentrated aqueous sodium chloride solution three times (250 ml each) and with saturated aqueous sodium chloride solution (250 ml) once. After drying over sodium sulfate all volatile materials are removed in vacuo to yield the title compound as a solid which is used without further purification.

후처리

  1. customthe temperature below 10° C
  2. temperatureThe reaction mixture is cooled to 0° C. again
  3. customthe temperature below 10° C
  4. waitAfter 15 min at 0° C.
  5. customThe organic layer is separated
  6. extractionthe aqueous layer is extracted with THF three times (124 ml each)
  7. washThe combined organic layers are washed with half concentrated aqueous sodium chloride solution three times (250 ml each) and with saturated aqueous sodium chloride solution (250 ml) once
  8. dry with materialAfter drying over sodium sulfate all volatile materials
  9. customare removed in vacuo

출처 및 근거

ORD 기록
ord-065756a0eb404d13970046f699027178
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018175B2

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