Water → HCID 40503070, 화합물

HRID 2096916노트

반응식

HRID 2096916 반응식
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C(=O)([O-])[O-].[K+].[K+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C(#N)C>[CH2:14]([N:1]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@H:2]([CH2:3][OH:4])[C:5]([O:7][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 71077D-Serine

생성물 1

HCID 40503070HCID 40503070, 화합물수율 88.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

D-serine (10.5 g, 0.1 mol) was stirred with potassium carbonate (69 g, 0.5 mol), benzyl bromide (64.8 g, 0.375 mol) and water (10 mL) in acetonitrile (250 mL) at 55° C. for 24 hours. The reaction mixture was filtered and washed with ethyl acetate. The filtrate was concentrated with silica gel. The product was purified by column chromatography, eluting with 5-20% ethyl acetate in hexanes to give benzyl (2R)-2-(dibenzylamino)-3-hydroxypropanoate (33.36 g, 88%) as a pale-yellow sticky oil. 1H NMR (300 MHz, CDCl3): (ppm) 7.20-7.44 (m, 15H), 5.27 (q, 2H), 3.91 (d, 2H), 3.80 (m, 2H), 3.67 (d, 2H), 3.63 (m, 1H) and 2.52 (dd, 1H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated with silica gel
  4. customThe product was purified by column chromatography
  5. washeluting with 5-20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-1fdc296be4a24db2a21b39438a0df130
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450336B2

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