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

HRID 1775831ノート

反応式

HRID 1775831 の反応式
[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]

参加物

5

反応物 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)

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4383e591810a4a0db9aa407d477f2444
出典データセット
uspto-grants-2016_02
特許番号
US09260427B2

反応ノート

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