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3,4-Dichlorobenzaldehyde → ethyl 2-(3-(3,4-dichlorobenzylamino)propyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

HRID 579543
ノート
印刷プレビュー

反応式

HRID 579543 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.Cl.[NH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:35]([CH3:39])[C:36](=[O:38])[CH3:37])([CH2:22][CH2:23][CH2:24][CH2:25][B:26]1[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]1)[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH:12][CH2:13][CH2:14][CH2:15][C:16]([N:35]([CH3:39])[C:36](=[O:38])[CH3:37])([CH2:22][CH2:23][CH2:24][CH2:25][B:26]1[O:30][C:29]([CH3:31])([CH3:32])[C:28]([CH3:33])([CH3:34])[O:27]1)[C:17]([O:19][CH2:20][CH3:21])=[O:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 227103,4-DichlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66832929ethyl 2-(3-aminopropyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate hydrochloride

生成物 1

HCID 66832776ethyl 2-(3-(3,4-dichlorobenzylamino)propyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate収率 53.8%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

A solution of 3,4-dichlorobenzaldehyde (55 mg, 0.31 mmol) and ethyl 2-(3-aminopropyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate hydrochloride (120 mg, 0.26 mmol) in dichloromethane (3 mL) was stirred at room temperature. After 30 min, sodium triacetoxyborohydride (138 mg, 0.65 mmol) was added in one portion and stirring was continuated overnight. Once complete, the solution was diluted with dichloromethane (10 mL), quenched with aq 5% NaHCO3 (W/V, 5 mL) and stirred vigorously for 30 min. The layers were separated and the organic phase was washed with water and sat'd aq sodium chloride, dried over MgSO4, filtered and concentrated. Purification by flash column chromatography (2-20% methanol in dichloromethane) gave ethyl 2-(3-(3,4-dichlorobenzylamino)propyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (78 mg). ESI MS found for C27H43BCl2N2O5 m/z [557.6/559.6 (M+1)].

後処理

  1. waitwas continuated overnight
  2. customquenched with aq 5% NaHCO3 (W/V, 5 mL)
  3. stirringstirred vigorously for 30 min
  4. customThe layers were separated
  5. washthe organic phase was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography (2-20% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-408610fb4a78450db2c62668b4e58c30
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040703B2

反応ノート

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