Potassium Carbonate → (R)-methyl 6-oxo-5,6,6a,7,9,10-hexahydropyrido[3,2-e][1,4]thiazino[4,3-a]pyrazine-3-carboxylate

HRID 69659

反応式

HRID 69659 の反応式
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][C@H:2]1[C:7]([OH:9])=O.Cl[C:11]1[C:20]([N+:21]([O-])=O)=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C(Cl)Cl.[Pt].[NH4+].[O-][V](=O)=O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>[O:9]=[C:7]1[NH:21][C:20]2[CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[N:12][C:11]=2[N:1]2[CH2:6][CH2:5][S:4][CH2:3][C@@H:2]12

参加物

9

反応物 3

HCID 11430Potassium CarbonateHCID 346961Methyl 6-chloro-5-nitronicotinateHCID 1152541(R)-thiomorpholine-3-carboxylic acid

生成物 1

HCID 58324497(R)-methyl 6-oxo-5,6,6a,7,9,10-hexahydropyrido[3,2-e][1,4]thiazino[4,3-a]pyrazine-3-carboxylate収率 52%

試薬・触媒・溶媒 5

HCID 7540Triphenyl phosphite触媒HCID 23939Platinum触媒HCID 516859Ammonium metavanadate触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of (R)-thiomorpholine-3-carboxylic acid (1.009 g, 6.86 mmol) in THF was added methyl 6-chloro-5-nitronicotinate (1.35 g, 6.23 mmol) and potassium carbonate (2.58 g, 18.70 mmol). The suspension was heated to reflux for 3 hours. The crude orange solution was allowed to cool to RT and filtered through a pad of celite which was washed with DCM (50 mL), and transferred to a bomb hydroginator. To the solution was added triphenyl phosphite (0.019 ml, 0.061 mmol), platinum (0.238 g, 0.061 mmol), and ammonium metavanadate. The vessel was sealed and pressurized to 140 psi with stirring for 24 h at room temperature. The vessel was depressurized and the mixture was diluted with DCM (100 mL) and refluxed for 30 minutes. The hot mixture was filtered through celite and concentrated to yield 887 mg (52%) of the product as a white solid. [M+H] calc'd for C12H13N3O3S, 280; found, 280.

後処理

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered through a pad of celite which
  4. washwas washed with DCM (50 mL)
  5. customThe vessel was sealed
  6. temperaturerefluxed for 30 minutes
  7. filtrationThe hot mixture was filtered through celite and
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-96ba58f6cfed4f7c9bc3834662e899d6
出典データセット
uspto-grants-2014_09
特許番号
US08822470B2

関連ノート

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