Dabco → Methyl N-triphenylmethyl-O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serinate

HRID 1265220노트

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HRID 1265220 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C@@H:16]([C:37]([O:39][CH3:40])=[O:38])[NH:17][C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:41]([N:44]=[C:45]=[O:46])[CH2:42][CH3:43].N12CCN(CC1)CC2>C1(C)C=CC=CC=1>[C:25]1([C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:17][C@H:16]([C:37]([O:39][CH3:40])=[O:38])[CH2:15][O:14][C:10]2[CH:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:45]([NH:44][CH2:41][CH2:42][CH3:43])=[O:46])[CH:3]=3)[CH:13]=[CH:12][CH:11]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

5

반응물 3

HCID 9237DabcoHCID 61033Propyl isocyanateHCID 11353040Methyl O-(3'-amino-1,1'-biphenyl-3-yl)-N-triphenylmethyl-L-serinate

생성물 1

HCID 11215663Methyl N-triphenylmethyl-O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serinate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Methyl O-(3′-amino-1,1′-biphenyl-3-yl)-N-triphenylmethyl-L-serinate (Example 2) (250.0 mg, 0.47 mmol, 1 equiv) was dissolved in toluene (5 mL) and treated at rt with n-propyl isocyanate (402.5 mg, 4.73 mmol, 10 equiv) and DABCO (1,4-diazabicyclo[2,2,2]octane) (5.3 mg, 0.05 mmol, 0.1 equiv). The reaction mixture was stirred at rt for 14 h and then partitioned between toluene and sat. aqueous NH4Cl solution. The organic layer was separated and dried over NaSO4 and the solvents were removed in vacuuo. The crude product was titurated with petroleum ether to give a yellow solid. Yield 210.0 mg, 72.4%. 1H NMR (CDCl3, 200 MHz) δ 7.65-7.50 (m, 9H); 7.40-7.15 (m, 12H); 6.95 (d, 2H); 5.19-4.98 (m, 1H); 4.25 (dd, 1H); 4.03 (dd, 1H); 3.38-3.02 (m, 4H); 2.88 (d, 1H); 1.65-1.45 (m, 2H); 0.90 (t, 3H). MS (EI) 614 (M+H), 243 (CPh3).

후처리

  1. custompartitioned between toluene and sat. aqueous NH4Cl solution
  2. customThe organic layer was separated
  3. dry with materialdried over NaSO4
  4. customthe solvents were removed in vacuuo
  5. customto give a yellow solid

출처 및 근거

ORD 기록
ord-7dd89d0b80dc459a825484d2a49b47d3
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545029B2

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