Diisopropylethylamine → (Tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-1,1-dimethyl-ethoxycarbonylamino)-acetic acid

HRID 2405801

反応式

HRID 2405801 の反応式
[NH2:1][CH:2]([CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4].[F:12][C:13]([F:31])([F:30])[C:14]([O:17][C:18](=O)[O:19]C1C=CC([N+]([O-])=O)=CC=1)([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>CC#N.O>[O:9]1[CH2:8][CH2:7][CH:6]([CH:2]([NH:1][C:18]([O:17][C:14]([CH3:16])([CH3:15])[C:13]([F:31])([F:30])[F:12])=[O:19])[C:3]([OH:5])=[O:4])[CH2:11][CH2:10]1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 33855454'-TetrahydropyranylglycineHCID 577851834-Nitrophenyl 1,1,1-Trifluoro-2-Methylpropan-2-yl-carbonate

生成物 1

HCID 68797736(Tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-1,1-dimethyl-ethoxycarbonylamino)-acetic acid収率 70.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

Amino-(tetrahydro-pyran-4-yl)-acetic acid (80 mg, 0.5 mmol) was dissolved in CH3CN (5 mL) and H2O (1 mL), carbonic acid 4-nitro-phenyl ester 2,2,2-trifluoro-1,1-dimethyl-ethyl ester (175 mg, 0.6 mmol) and DIEA (88 μL, 0.5 mmol) were added slowly. The reaction was allowed to stir at room temperature for 16 h. After concentrated, diluted with EtOAc, washed with brine and H2O, dried over Na2SO4, the crude product was purified on silica (12 g, 25-75% EtOAc/hexanes) to give intermediate (tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-1,1-dimethyl-ethoxycarbonylamino)-acetic acid as light yellow solid (110 mg, 70%).

後処理

  1. concentrationAfter concentrated
  2. additiondiluted with EtOAc
  3. washwashed with brine and H2O
  4. dry with materialdried over Na2SO4
  5. customthe crude product was purified on silica (12 g, 25-75% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ff14b14949424741af5e1e472fba583b
出典データセット
uspto-grants-2014_08
特許番号
US08809267B2

関連ノート

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