Triphenylphosphine → (R)-N-(2,4-Dimethoxybenzyl)-3-(3-hydroxy-1-phenylpropyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

HRID 920272

反応式

HRID 920272 の反応式
[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[CH2:5][N:6]([C:20]1[S:24][N:23]=[CH:22][N:21]=1)[S:7]([C:10]1[CH:19]=[CH:18][C:13]2[NH:14][C:15](=[O:17])[O:16][C:12]=2[CH:11]=1)(=[O:9])=[O:8].[C:31]1([C@@H:37](O)[CH2:38][CH2:39][OH:40])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CCOC(C)=O.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[CH2:5][N:6]([C:20]1[S:24][N:23]=[CH:22][N:21]=1)[S:7]([C:10]1[CH:19]=[CH:18][C:13]2[N:14]([C@@H:37]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:38][CH2:39][OH:40])[C:15](=[O:17])[O:16][C:12]=2[CH:11]=1)(=[O:9])=[O:8]

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 6950537(1S)-1-phenylpropane-1,3-diolHCID 89526027N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

生成物 1

HCID 117629301(R)-N-(2,4-Dimethoxybenzyl)-3-(3-hydroxy-1-phenylpropyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

Accordingly, the compound of Formula 37-1 (N-(2,4-dimethoxybenzyl)-3-[(1R)-3-hydroxy-1-phenylpropyl]-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydro-1,3-benzoxazole-6-sulfonamide) was prepared from a solution provided by dissolving 200 mg of the compound of Formula 1-5 (0.429 mmol, prepared as described above) and (S)-1-phenylpropane-1,3-diol (65.3 mg, 0.429 mmol) (0.429 mmol) in 2 mL of THF. This solution was cooled to 0° C. and treated with triphenylphosphine (0.225 g, 0.858 mmol) followed by DEAD (0.136 mL, 0.858 mmol). After stirring at 0° C. for 120 min, the reaction mixture was diluted with EtOAc (50 mL) and saturated sodium bicarbonate (5 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by normal phase chromatography (10-80% EtOAc in hexane) yielded the compound of Formula 37-1 as a yellow oil which was used as isolated.

後処理

  1. customAccordingly, the compound of Formula 37-1 (N-(2,4-dimethoxybenzyl)-3-[(1R)-3-hydroxy-1-phenylpropyl]-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydro-1,3-benzoxazole-6-sulfonamide) was prepared from a solution
  2. customprovided
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by normal phase chromatography (10-80% EtOAc in hexane)

出典と根拠

ORDレコード
ord-14c7da05a8ef4826adb0e80b937486a6
出典データセット
uspto-grants-2016_03
特許番号
US09273040B2

関連ノート

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