4-Methylmorpholine → HCID 89827923、化合物

HRID 1051807

反応式

HRID 1051807 の反応式
[C:1]([NH:11][C@@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN1CCOCC1.[NH2:26][CH2:27][CH:28]([O:31][CH3:32])[O:29][CH3:30]>C1COCC1>[CH3:30][O:29][CH:28]([O:31][CH3:32])[CH2:27][NH:26][C:16](=[O:18])[C@H:12]([NH:11][C:1](=[O:2])[O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH:13]([CH3:14])[CH3:15]

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 712434N-alpha-Benzyloxycarbonyl-D-valine

生成物 1

HCID 89827923HCID 89827923、化合物収率 99.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

A solution of Cbz-D-Valine (500 g, 1.99 mol) and N-methylmorpholine (201.8 g, 1.99 mol) in anhydrous THF (8 L) was cooled to −15° C. and i-butyl chlorofomate (299 g, 2.19 mol) was added dropwise under stirring. After 30 min, a solution of 1-amino-2,2-dimethyoxyethane (209.5 g, 1.99 mol) in THF (1 L) was added slowly and the temperature was maintained at −15° C. for 2 h. The reaction mixture was washed with brine (2 L) and the organic phase was concentrated to remove the THF. The residue was diluted with EtOAc (4 L), washed with 1N aq HCl (2×2 L), sat. aq. NaHCO3 (2 L) and sat. aq. Na2CO3 (2 L) and brine (1.5 L). After drying over Na2SO4, the organic solvent was removed under reduce pressure to afford (R)-benzyl (1-((2,2-dimethoxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate as a white solid (670 g, yield 99.5%), which was used for next step without further purification. LC-MS m/z 360.9 [M+Na]+.

後処理

  1. additioni-butyl chlorofomate (299 g, 2.19 mol) was added dropwise
  2. washThe reaction mixture was washed with brine (2 L)
  3. concentrationthe organic phase was concentrated
  4. customto remove the THF
  5. additionThe residue was diluted with EtOAc (4 L)
  6. washwashed with 1N aq HCl (2×2 L), sat. aq. NaHCO3 (2 L) and sat. aq. Na2CO3 (2 L) and brine (1.5 L)
  7. dry with materialAfter drying over Na2SO4
  8. customthe organic solvent was removed

出典と根拠

ORDレコード
ord-bfee45d059e94e5285f666db0896a4f1
出典データセット
uspto-grants-2016_07
特許番号
US09388190B2

関連ノート

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