4-Methylmorpholine → tert-butyl((R)-1-furan-3-ylmethyl-2-hydroxy-ethyl)-carboxylate

HRID 1641358노트

반응식

HRID 1641358 반응식
N[C@H:2]([CH2:6][C:7]1[CH:11]=[CH:10][O:9][CH:8]=1)[C:3]([OH:5])=[O:4].C(OC(N[C@H]([CH2:24][C:25]1[CH:29]=CO[CH:26]=1)C(O)=O)=O)(C)(C)C.CN1CC[O:34][CH2:33]C1.C(OC(Cl)=O)C(C)C>C(COC)OC>[C:25]([O:5][C:3]([C@H:2]([CH2:6][C:7]1[CH:11]=[CH:10][O:9][CH:8]=1)[CH2:33][OH:34])=[O:4])([CH3:29])([CH3:26])[CH3:24]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 14797110(R)-2-Amino-3-(furan-3-yl)propanoic acidHCID 66736552(R)-2-tert-butoxycarbonylamino-3-furan-3-yl-propionic acid

생성물 1

HCID 66735629tert-butyl((R)-1-furan-3-ylmethyl-2-hydroxy-ethyl)-carboxylate

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
-30 °C

실험 절차

Starting from (R)-2-amino-3-furan-3-yl-propionic acid (DE3829451), (R)-2-tert-butoxycarbonylamino-3-furan-3-yl-propionic acid is prepared. Under argon 420 mg (R)-2-tert-butoxycarbonylamino-3-furan-3-yl-propionic acid are suspended in 2.5 ml dimethoxyethane suspended. The reaction mixture is cooled to −30° C. 220 μl N-methylmorpholine are added and then 240 μl isobutylchloroformate in 1.5 ml dimethoxyethane is added dropwise. The reaction mixture is allowed to come up to −5° C. and the precipitate is quickly filtered. The filtrate is cooled to −15° C. 100 mg sodium borohydride and a few drops of water are added. The reaction mixture is stirred for 1 hour at ambient temperature and evaporated to dryness. The residue is suspended in ethyl acetate. The reaction mixture is dried and evaporated to dryness. 370 mg of the product are obtained as a solid. Analytical HPLC-MS (method D): RT=1.21 min.

후처리

  1. customis prepared
  2. customto come up to −5° C.
  3. filtrationthe precipitate is quickly filtered
  4. temperatureThe filtrate is cooled to −15° C
  5. addition100 mg sodium borohydride and a few drops of water are added
  6. customevaporated to dryness
  7. customThe reaction mixture is dried
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-0988b71ab850420fa5866bd75843d29c
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114878B2

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