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Water → (R)-3-(3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenyl trifluoromethanesulfonate

HRID 2277035
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HRID 2277035 반응식
CCN(CC)CC.[OH:8][C@@H:9]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=1)[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].[O:27](S(C(F)(F)F)(=O)=O)[S:28]([C:31]([F:34])([F:33])[F:32])(=O)=[O:29].O>C(Cl)Cl>[F:32][C:31]([F:34])([F:33])[S:28]([O:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C@H:9]([OH:8])[CH2:10][CH2:11][NH:12][C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19])[CH:21]=1)(=[O:29])=[O:27]
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

생성물 1

HCID 90405606(R)-3-(3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenyl trifluoromethanesulfonate

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

Et3N (1.5 mL, 10.76 mmol) was added to a suspension of Intermediate I (1.00 g, 3.74 mmol) in anhydrous CH2Cl2 (20 mL), and a clear solution resulted. The reaction mixture was cooled to 0° C. under N2 and Tf2O (0.7 mL, 4.14 mmol) was added slowly via syringe. The reaction mixture was stirred for 2 h, water was added and the mixture was extracted with CH2Cl2 twice. Combined organic layers were washed with brine and concentrated under reduced pressure. Purification by flash chromatography (10%-50% EtOAc-hexanes gradient) gave (R)-3-(3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenyl trifluoromethanesulfonate as a colorless oil. Yield (1.10 g, 74%); 1H NMR (400 MHz, DMSO-d6); δ 7.45-7.52 (m, 1H), 7.39-7.43 (m, 1H), 7.33-7.38 (m, 1H), 7.27-7.32 (m, 1H), 6.72 (br. t, 1H), 5.45 (d, J=4.7 Hz, 1H), 4.56-4.66 (m, 1H), 2.86-3.2 (m, 2H), 1.60-1.70 (m, 2H), 1.33 (s, 9H).

후처리

  1. customa clear solution resulted
  2. extractionthe mixture was extracted with CH2Cl2 twice
  3. washCombined organic layers were washed with brine
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (10%-50% EtOAc-hexanes gradient)

출처 및 근거

ORD 기록
ord-80834f987a8149a183503c4db0d9582d
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133154B2

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