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Cesium carbonate → HCID 68621706、化合物

HRID 2215280
ノート
印刷プレビュー

反応式

HRID 2215280 の反応式
[ClH:1].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][C:5]=1[O:15][CH2:16][C@H:17]([OH:33])[CH2:18][NH:19][C:20]([CH3:32])([CH3:31])[CH2:21][CH:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1)#[N:3].C(=O)([O-])[O-].[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1.I[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66]>CN(C=O)C>[ClH:1].[CH2:59]([O:13][C:12](=[O:14])[CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]#[N:3])=[C:5]([O:15][CH2:16][C@H:17]([OH:33])[CH2:18][NH:19][C:20]([CH3:31])([CH3:32])[CH2:21][CH:22]2[CH2:23][C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:30]2)[CH:6]=1)[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 123801-IodooctaneHCID 2855718-Crown-6HCID 68607251Benzenepropanoic acid, 4-cyano-3-((2R)-3-((2-(2,3-dihydro-1H-inden-2-yl)-1,1-dimethylethyl)amino)-2-hydroxypropoxy)-, hydrochloride (1:1)

生成物 1

HCID 68621706HCID 68621706、化合物

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
70 °C

実験手順

A solution of the compound from Example 5 (100 mg, 0.2 mmol) in dry DMF (15 mL) was treated with cesium carbonate (141 mg, 0.4 mmol) and 18-crown-6 (100 mg, 0.41 mmol) followed by 1-iodooctane (144 mg, 0.6 mmol). The resulting mixture was heated at 70° C. under argon for 20 h. The reaction was cooled, concentrated and the residue partitioned between water and ethyl acetate. The organic layer was washed with 10% Na2CO3 (aqueous), brine, dried over MgSO4 and evaporated. Purification by flash chromatography (4% MeOH in CH2Cl2) gave the ester as a yellow oil. The oil in ether was treated with HCl and filtered to give the above titled compound (50 mg, 46%). LC-MS m/e 549.4 [M+H]+.

後処理

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customthe residue partitioned between water and ethyl acetate
  4. washThe organic layer was washed with 10% Na2CO3 (aqueous), brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customPurification by flash chromatography (4% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-81a73694f1fa4757991edb46ab587d38
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07109238B2

反応ノート

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