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

HRID 1265220ノート

反応式

HRID 1265220 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7dd89d0b80dc459a825484d2a49b47d3
出典データセット
uspto-grants-2003_04
特許番号
US06545029B2

反応ノート

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