Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(2-carbamoylthiophen-3-ylamino)-2-phenylacetate

HRID 469450ノート

反応式

HRID 469450 の反応式
[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[NH:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12])(=[O:3])[NH2:2].[N:20]12[CH2:27][CH2:26][CH:23]([CH2:24][CH2:25]1)[C@@H:22](O)[CH2:21]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[NH:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([O:13][C@@H:22]1[CH:23]2[CH2:26][CH2:27][N:20]([CH2:25][CH2:24]2)[CH2:21]1)=[O:12])(=[O:3])[NH2:2]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 585569892-(2-Carbamoylthiophen-3-ylamino)-2-phenylacetic acid

生成物 1

HCID 54763973(R)-quinuclidin-3-yl 2-(2-carbamoylthiophen-3-ylamino)-2-phenylacetate収率 6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-(2-carbamoylthiophen-3-ylamino)-2-phenylacetic acid (I7) (389 mg, 1.41 mmol), (R)-quinuclidin-3-ol (215 mg, 1.69 mmol), DCC (349 mg, 1.69 mmol) and HOBT (259 mg, 1.69 mmol) in dry THF (5 ml) was stirred at room temperature overnight. THF was evaporated, and the crude product was taken up with EtOAc and washed twice with 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by preparative HPLC. The fractions with the product are combined and evaporated to dryness. The residue was dissolved in 2M K2CO3 and extracted twice with EtOAc to obtain (R)-quinuclidin-3-yl 2-(2-carbamoylthiophen-3-ylamino)-2-phenylacetate (32 mg, 6% yield).

後処理

  1. customTHF was evaporated
  2. washwashed twice with 2M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by preparative HPLC
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in 2M K2CO3
  9. extractionextracted twice with EtOAc

出典と根拠

ORDレコード
ord-ce04655f38de48979470b15eda76ccc0
出典データセット
uspto-grants-2014_01
特許番号
US08629160B2

反応ノート

読み込み中…