Triethylamine → Tert-butyl 4-(5-methylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

HRID 1689474노트

반응식

HRID 1689474 반응식
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.[O:26]1[C:31]2([CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]2)[CH2:30][NH:29][CH2:28][CH2:27]1.[CH3:44][C:45]1[S:49][CH:48]=[C:47]([C:50](O)=[O:51])[CH:46]=1.C(N(CC)CC)C>CN(C=O)C.[Cl-].[Na+].O>[CH3:44][C:45]1[S:49][CH:48]=[C:47]([C:50]([N:29]2[CH2:30][C:31]3([CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]3)[O:26][CH2:27][CH2:28]2)=[O:51])[CH:46]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 2090693-Thiophenecarboxylic acid, 5-methyl-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66964240Tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride

생성물 1

HCID 57989109Tert-butyl 4-(5-methylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.91 g) was added to a solution of tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (WuXi PharmaTech) (0.5 g), 5-methyl-thiophene-3-carboxylic acid (0.243 g) and triethylamine (0.95 mL) in DMF (10 mL) and the resulting mixture stirred for 16 h. The reaction mixture was poured into brine (40 mL) and extracted with ethyl acetate (3×50 mL). The combined organic solutions were washed with water (150 mL), brine (150 mL), dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with 0-10% methanol in dichloromethane to give the subtitled compound as a clear oil. Yield 0.34 g.

후처리

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic solutions were washed with water (150 mL), brine (150 mL)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification
  7. washeluting with 0-10% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-22c27b8020d6461db83900240eff563d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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