Dimethylamine → Tert-butyl 1-(dimethylamino)-3-(3-hydroxyphenyl)-1-oxopropan-2-ylcarbamate

HRID 449506ノート

反応式

HRID 449506 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.[CH3:28][N+:29](C)=[C:30](N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CNC.C1COCC1>CN(C)C=O.C(OCC)(=O)C>[CH3:28][N:29]([CH3:30])[C:10](=[O:11])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1

参加物

8

反応物 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 13890118Boc-DL-m-tyrosine

生成物 1

HCID 59496639Tert-butyl 1-(dimethylamino)-3-(3-hydroxyphenyl)-1-oxopropan-2-ylcarbamate収率 78%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoic acid (0.89 g, 3.1 mol) was treated with N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1.8 g, 4.6 mmol), N,N-diisopropylethylamine (1.6 mL, 9.3 mmol) and 2 M dimethylamine in THF (3.0 mL, 6.0 mmol), in N,N-dimethylformamide (20 mL) at r.t. The reaction was complete after stirring for 2 h. This was taken up in ethyl acetate and washed with 1 N HCl, brine, dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as an oily residue. The product was purified by flash chromatography on a silica gel column eluting hexane: ethyl acetate gradient to give tert-butyl 1-(dimethylamino)-3-(3-hydroxyphenyl)-1-oxopropan-2-ylcarbamate (0.75 g, 78%) as an off white solid. Analytical LCMS (M+H-Boc)+: m/z=208.9.

後処理

  1. washwashed with 1 N HCl, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give the crude product as an oily residue
  5. customThe product was purified by flash chromatography on a silica gel column
  6. washeluting hexane

出典と根拠

ORDレコード
ord-85006732622d40ab93b0372af5582b0e
出典データセット
uspto-grants-2013_07
特許番号
US08481732B2

反応ノート

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