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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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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
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HRID 579543 반응식
[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]
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참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

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)].

후처리

  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)

출처 및 근거

ORD 기록
ord-408610fb4a78450db2c62668b4e58c30
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040703B2

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