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Trifluoroacetic acid → (3R)-3-({[(1S)-2,2-Dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoic acid

HRID 1700979
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HRID 1700979 반응식
FC(F)(F)C(O)=O.[CH3:8][C:9]([CH3:52])([CH3:51])[C@H:10]([NH:22][C:23]([C@H:25]([CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[C:39]([CH3:50])[CH:38]=1)[CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[O:24])[C:11]([NH:13][C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])=[O:12]>ClCCl>[CH3:51][C:9]([CH3:8])([CH3:52])[C@H:10]([NH:22][C:23]([C@H:25]([CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[C:39]([CH3:50])[CH:38]=1)[CH2:26][C:27]([OH:29])=[O:28])=[O:24])[C:11]([NH:13][C@@H:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:15])=[O:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 59875747tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoate

생성물 1

HCID 57238483(3R)-3-({[(1S)-2,2-Dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoic acid수율 127.3%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

Trifluoroacetic acid (2.5 mL) was added dropwise over 5 min to a stirred solution of tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoate (550 mg, 0.9 mmol) in anhydrous dichloromethane (5 mL) under nitrogen at 20° C. The solution was stirred for 1 h and concentrated under reduced pressure. The residue was diluted with hydrochloric acid (2M) and extracted with three portions of ethyl acetate. The combined organic solutions were washed with saturated aqueous sodium chloride, dried (MgSO4) and concentrated under reduced pressure. Two portions of toluene were added and evaporated to give the title compound as a yellow gum (640 mg), contaminated with toluene and trifluoroacetic acid.

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with hydrochloric acid (2M)
  3. extractionextracted with three portions of ethyl acetate
  4. washThe combined organic solutions were washed with saturated aqueous sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. additionTwo portions of toluene were added
  8. customevaporated

출처 및 근거

ORD 기록
ord-203665f429094eda99db637cf707d8af
출처 데이터셋
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06350907B1

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