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

HRID 1508278ノート

反応式

HRID 1508278 の反応式
[NH2:1][C:2](=O)[C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C)C=O>[C:2]([C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4])#[N:1]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-dd77eb606b1140678a9674ffd9f7b3b1
出典データセット
uspto-grants-2015_12
特許番号
US09221824B2

反応ノート

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