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Triethylamine → tert-butyl 4(S)-(2(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate

HRID 507831
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HRID 507831 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O.C(N(CC)CC)C.[NH2:23][CH2:24][C@H:25]([CH:42]([CH3:44])[CH3:43])[CH2:26][C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].[OH-].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH:23][CH2:24][C@H:25]([CH:42]([CH3:44])[CH3:43])[CH2:26][C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 176069102-(3-Methoxypropoxy)benzoic acidHCID 68623939tert-butyl 4(S)-(2(S)-aminomethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate

생성물 1

HCID 68624344tert-butyl 4(S)-(2(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

The solution of 2.99 g of 2-(3-methoxypropoxy)benzoic acid [179992-98-4] and 3.95 ml of triethylamine in 60 ml of dichloromethane is cooled to 15° C. and admixed with 3.70 g of bis-(2-oxo-3-oxazolidynyl)phosphinoyl chloride. The mixture is stirred over 1 hour and subsequently admixed with the solution of 2.22 g of tert-butyl 4(S)-(2(S)-aminomethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate in 3 ml of dichloromethane and 0.703 g of 4-dimethylaminopyridine, and stirred overnight. The reaction mixture is poured onto 1M NaOH and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly yellowish oil. Rf=0.29 (1:1 EtOAc-heptane); Rt=5.49 (gradient I).

후처리

  1. stirringstirred overnight
  2. extractionextracted with tert-butyl methyl ether (2×)
  3. washThe combined organic phases are washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-9eb4e79809184ddc90686a7e7421ffff
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786307B2

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