Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(4-chlorophenylamino)-2-phenylacetate

HRID 1044041

反応式

HRID 1044041 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:44]12[CH2:51][CH2:50][CH:47]([CH2:48][CH2:49]1)[C@@H:46](O)[CH2:45]2>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:10]([O:12][C@@H:46]2[CH:47]3[CH2:50][CH2:51][N:44]([CH2:49][CH2:48]3)[CH2:45]2)=[O:11])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 305145(4-Chloro-phenylamino)-phenyl-acetic acid

生成物 1

HCID 46840420(R)-quinuclidin-3-yl 2-(4-chlorophenylamino)-2-phenylacetate収率 37.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(4-chlorophenylamino)-2-phenylacetic acid (I11) (574 mg, 2.20 mmol) in dry THF (20 ml), were added DCC (543 mg, 2.64 mmol), HOBt (359 mg, 2.64 mmol), and 3(R)-quinuclidinol (558 mg, 4.40 mmol). The resulting mixture was stirred at RT overnight (UPLC-MS monitoring: complete conversion). The solvent was evaporated, and the residue was partitioned between EtOAc and 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The resulting crude was purified by flash chromatography (DCM/MeOH=99/1 to 85/15) to obtain the title compound (306 mg, 37% yield, mixture of diastereomers).

後処理

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between EtOAc and 2M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting crude was purified by flash chromatography (DCM/MeOH=99/1 to 85/15)

出典と根拠

ORDレコード
ord-73fcd8624b4848568cea578149a9d504
出典データセット
uspto-grants-2013_10
特許番号
US08563577B2

関連ノート

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