5-Tert-butylthiophene-2-carboxylic acid → tert-butyl (5-(tert-butyl)thiophene-2-carbonyl)-L-tyrosinate

HRID 1623010노트

반응식

HRID 1623010 반응식
[C:1]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:37][C@@H:38]([CH2:46][C:47]1[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=1)[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>CN(C=O)C>[C:1]([C:5]1[S:9][C:8]([C:10]([NH:37][C@H:38]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:46][C:47]2[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=2)=[O:12])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 4583495-Tert-butylthiophene-2-carboxylic acidHCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 86689678tert-butyl (5-(tert-butyl)thiophene-2-carbonyl)-L-tyrosinate수율 89.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Prepared using General Procedure 7. Into a solution of 5-(tert-butyl)thiophene-2-carboxylic acid (1.93 g, 10.0 mmol) in DMF (20 mL) were added HATU (4.56 g, 12.0 mmol) and TEA (4.18 mL, 30.0 mmol). The mixture was stirred at room temperature for 30 min and (S)-tert-butyl 2-amino-3-(4-hydroxyphenyl)propanoate (2.37 g, 10.0 mmol) was added. After 1 h, the reaction mixture was poured into 400 mL of ice-water and the solid was filtered. The solid was dissolved in DCM and EA, dried over MgSO4, concentrated, and purified by chromatography (EA/hexanes) to provide 3.6 g (89%) of tert-butyl (5-(tert-butyl)thiophene-2-carbonyl)-L-tyrosinate. LCMS-ESI (m/z) calculated for C22H29NO4S: 403.2; found: 426.1 [M+Na]+, tR=9.07 min (Method 2).

후처리

  1. customPrepared
  2. waitAfter 1 h
  3. filtrationthe solid was filtered
  4. dissolutionThe solid was dissolved in DCM
  5. dry with materialEA, dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by chromatography (EA/hexanes)

출처 및 근거

ORD 기록
ord-d74c2aa41b564ae6aceeb57e81ec1ea2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778923B2

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