Water → tert-butyl N-((1S)-1-cyanoethyl)carbamate

HRID 452036노트

반응식

HRID 452036 반응식
[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]([CH3:12])[C:9]([NH2:11])=O)([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C)C=O>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]([C:9]#[N:11])[CH3:12])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 7015295Boc-Ala-NH2

생성물 1

HCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamate수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of tert-butyl[(1S)-2-amino-1-methyl-2-oxoethyl]carbamate (Step 1, 0.7 g, 0.004 mol) in N,N-dimethylformamide (5 mL) was added 343 mg of cyanuric chloride (0.00186 mol) at once. The reaction mixture was stirred for 4 h. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with EtOAc in hexane (30-50%) to yield the desired product (400 mg, 63%). 1H-NMR (300 MHz, DMSO-d6): 7.74 (d, J=7.0 Hz, 1H), 4.48 (m, 1H), 1.40 (s, 9H), 1.35 (d, J=7.0 Hz, 3H).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on a silica gel column with EtOAc in hexane (30-50%)

출처 및 근거

ORD 기록
ord-e23b8298f3a748a7b362acbe3f79ff7f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487096B2

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