4-Methylmorpholine → HCID 89827923, 화합물

HRID 1051807

반응식

HRID 1051807 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 89827923HCID 89827923, 화합물수율 99.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-15 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-bfee45d059e94e5285f666db0896a4f1
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388190B2

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