Triethylamine → HCID 67274143、化合物

HRID 599767ノート

反応式

HRID 599767 の反応式
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:36](O)=[O:37])[CH2:19][C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:22]([CH3:35])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=2[NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[N:72]1([CH:78]2[CH2:83][CH2:82][N:81]([CH2:84][C:85]([O:87][CH2:88][CH3:89])=[O:86])[CH2:80][CH2:79]2)[CH2:77][CH2:76][NH:75][CH2:74][CH2:73]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:21]=[C:22]([CH3:35])[C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:24]([CH3:26])[CH:25]=3)[C:36]([N:75]3[CH2:76][CH2:77][N:72]([CH:78]4[CH2:83][CH2:82][N:81]([CH2:84][C:85]([O:87][CH2:88][CH3:89])=[O:86])[CH2:80][CH2:79]4)[CH2:73][CH2:74]3)=[O:37])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=2[NH:3]1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 25208036(R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylateHCID 54188692HCID 54188692、化合物

生成物 1

HCID 67274143HCID 67274143、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2.80 g (4.90 mmol) (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 1g), 1.80 g (5.61 mmol) TBTU and 3.10 mL (22.08 mmol) triethylamine in 30 mL DMF was stirred for 1 h at RT. Then 2.00 g (5.48 mmol) ethyl (4-piperazin-1-yl-piperidin-1-yl)-acetate were added. The reaction mixture was stirred for 1 h at RT, poured onto 150 mL 15% K2CO3 solution and extracted with 200 mL EtOAc. The organic phase was extracted with 150 mL of 10% citric acid solution, the aqueous phase was made alkaline with 15% K2CO3 solution and extracted with 200 mL EtOAc. The organic phase was concentrated by evaporation i.vac. and the residue was purified by chromatography (silica gel, EtOH).

後処理

  1. extractionextracted with 200 mL EtOAc
  2. extractionThe organic phase was extracted with 150 mL of 10% citric acid solution
  3. extractionextracted with 200 mL EtOAc
  4. concentrationThe organic phase was concentrated by evaporation i.vac
  5. customand the residue was purified by chromatography (silica gel, EtOH)

出典と根拠

ORDレコード
ord-8fe1cc7a4a404a8eb5babb22b37465e8
出典データセット
uspto-grants-2011_03
特許番号
US07897603B2

反応ノート

読み込み中…