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

HRID 2405801노트

반응식

HRID 2405801 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ff14b14949424741af5e1e472fba583b
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809267B2

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