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

HRID 354497노트

반응식

HRID 354497 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f7cc9b8ba626427eb2a18da97491029c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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