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Diisopropylethylamine → tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate

HRID 2389334
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HRID 2389334 반응식
Cl.[NH2:2][C@@H:3]([CH2:8][OH:9])[C:4]([O:6][CH3:7])=[O:5].[C:10]([O:14][C:15]([N:17]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([C:26](O)=[O:27])[C:20]=2[CH:19]=[CH:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)C(C)C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C.O>[OH:9][CH2:8][C@H:3]([NH:2][C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[CH:19]=[CH:18][N:17]2[C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])=[O:27])[C:4]([O:6][CH3:7])=[O:5]
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참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 497588501-Boc-4-carboxyindole

생성물 1

HCID 68536502tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate수율 72.8%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (1.25 g), 1-(tert-butoxycarbonyl)-1H-indole-4-carboxylic acid (2.10 g) and N-ethyl-N-isopropyl-2-propanamine (2.94 mL) in DMF (25.0 mL) was added dropwise DPPA (1.91 mL) at 0° C. and the mixture was stirred at ambient temperature for 3 days. The resulting mixture was diluted with water (50.0 mL) and extracted with EtOAc (75 mL). The organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution. and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=99:1) to afford tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate (2.12 g) as a colorless syrup.

후처리

  1. extractionextracted with EtOAc (75 mL)
  2. washThe organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution
  3. dry with materialand brine, dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=99:1)

출처 및 근거

ORD 기록
ord-34eb15dc93cc451596386ad354cc21ed
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08273745B2

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