Diisopropylethylamine → methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alanylglycinate

HRID 1972389ノート

反応式

HRID 1972389 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:45][O:46][C:47](=[O:50])[CH2:48][NH2:49].CCN(C(C)C)C(C)C>O.CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([NH:49][CH2:48][C:47]([O:46][CH3:45])=[O:50])=[O:19])[CH2:10][CH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 7168106(S)-2-((t-Butoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propanoic acidHCID 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 66582350methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alanylglycinate収率 76.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A 100 mL round-bottomed flask was charged with N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-alanine (3.11 g, 11.38 mmol, Acros/Fisher Scientific, Waltham, Mass.), HATU (5.41 g, 14.22 mmol, Oakwood, West Columbia, S.C.), glycine methyl ester hydrochloride (1.714 g, 13.65 mmol, Sigma-Aldrich, St. Louis, Mo.), and 10 mL of DMF. To this was added Hünig's base (4.37 mL, 25.03 mmol). After 30 min at room temperature, the mixture was diluted with water (100 mL) and extracted with EtOAc (2×200 mL). The layers were separated and the organic extracts were washed with water (2×100 mL) and brine (50 mL), dried (MgSO4) and concentrated to give methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-alanylglycinate (3.00 g) as a yellow oil

後処理

  1. extractionextracted with EtOAc (2×200 mL)
  2. customThe layers were separated
  3. washthe organic extracts were washed with water (2×100 mL) and brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-58b144b09d0540ca94a90a2d791b4272
出典データセット
uspto-grants-2013_04
特許番号
US08431563B2

反応ノート

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