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Formic Acid → 1-(Tert-butyl) 3-methyl 3-formamidopyrrolidine-1,3-dicarboxylate

HRID 1038095
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HRID 1038095 반응식
[CH:1](O)=[O:2].[CH3:4][O:5][C:6]([C:8]1([NH2:20])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1)=[O:7].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1>CN(C1C=CN=CC=1)C>[CH3:4][O:5][C:6]([C:8]1([NH:20][CH:1]=[O:2])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:9]1)=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 576862811-Tert-butyl 3-methyl 3-aminopyrrolidine-1,3-dicarboxylate

생성물 1

HCID 576860951-(Tert-butyl) 3-methyl 3-formamidopyrrolidine-1,3-dicarboxylate

시약·촉매·용매 1

HCID 14284
4-(Dimethylamino)pyridine
촉매

실험 절차

Added formic acid (200 mg, 4.34 mmol) to solution of 3-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (1T) (900 mg, 3.688 mmol); 2-Chloro-4,6 dimethoxy-1,3,5-Triazine (CDMT) (800 mg, 4.556 mmol); DMAP (20 mg), and NMM (400 mg, 4 mmol) at room temperature, then stirred overnight. The solvent was evaporated and the residue extracted with MeCl2 (200 ml), washed with H2O (50 ml), dried over MgSO4, filtered and solvent evaporated yielding a solid which chromatographed on silica gel eluting with 5% MeOH/MeCl2 containing 2% NH4OH yielding 2T as a white solid (725 mg, 72%) LCMS (MH 273) Retention time=2.53 minutes.

후처리

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with MeCl2 (200 ml)
  3. washwashed with H2O (50 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customyielding a solid which
  8. customchromatographed on silica gel eluting with 5% MeOH/MeCl2 containing 2% NH4OH yielding 2T as a white solid (725 mg, 72%) LCMS (MH 273) Retention time=2.53 minutes

출처 및 근거

ORD 기록
ord-8a581bbb284949beaed372b5c7576a7d
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546404B2

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