1,2-Dichloroethane → methyl (S)-3-chloro-4-[2-[N-methyl-N-[3-methoxy-[N'-(2-fluorophenyl)ureido]phenylacetyl]amino]-1-propoxy]benzoate

HRID 354497ノート

反応式

HRID 354497 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])=[O:15])[C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][C:34]=1[O:35][CH2:36][C@@H:37]([NH:39][CH3:40])[CH3:38])[C:28]([O:30][CH3:31])=[O:29].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[Cl:24][C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][C:34]=1[O:35][CH2:36][C@@H:37]([N:39]([CH3:40])[C:10](=[O:12])[CH:9]([NH:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])=[O:15])[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:38])[C:28]([O:30][CH3:31])=[O:29]

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 698204933-methoxy-[N'-(2-fluorophenyl)ureido]phenylacetic acidHCID 86587798methyl (S)-3-chloro-4-(2-methylamino-1-propoxy)benzoate

生成物 1

HCID 86587797methyl (S)-3-chloro-4-[2-[N-methyl-N-[3-methoxy-[N'-(2-fluorophenyl)ureido]phenylacetyl]amino]-1-propoxy]benzoate収率 100.2%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-methoxy-[N′-(2-fluorophenyl)ureido]phenylacetic acid (296 mg, 0.93 mmol), methyl (S)-3-chloro-4-(2-methylamino-1-propoxy)benzoate (240 mg, 0.93 mmol), EDC (hydrochloride) (268 mg, 1.40 mmol), HOBt (189 mg, 1.40 mmol), and DMAP (23 mg, 0.19 mmol) in DMF (8 mL) was stirred at room temp for 1.5 hr. The mixture was diluted with EtOAc, washed with 0.5 N HCl, brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica-gel with 5% MeOH in CHCl3 as eluent to give 520 mg (100%) methyl (S)-3-chloro-4-[2-[N-methyl-N-[3-methoxy-[N′-(2-fluorophenyl)ureido]phenylacetyl]amino]-1-propoxy]benzoate as a red-brown amorphous solid.

後処理

  1. washwashed with 0.5 N HCl, brine
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica-gel with 5% MeOH in CHCl3 as eluent

出典と根拠

ORDレコード
ord-f7cc9b8ba626427eb2a18da97491029c
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

反応ノート

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