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3-Amino-3-Oxopropanoic Acid → (5S,7S)-5-(4-Cyanobenzyl)-3-(3,5-dichlorophenyl)-7-[(2-carbamoylacetyl)amino]-1,3-diazabicyclo[3.3.0]octane-2,4-dione

HRID 2223332
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HRID 2223332 반응식
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][C@@:8]23[CH2:15][C@H:14]([NH2:16])[CH2:13][N:12]2[C:11](=[O:17])[N:10]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:9]3=[O:26])=[CH:5][CH:4]=1)#[N:2].[C:29](O)(=[O:34])[CH2:30][C:31]([NH2:33])=[O:32].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1.C(Cl)CCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C@@:8]23[CH2:15][C@H:14]([NH:16][C:29](=[O:34])[CH2:30][C:31](=[O:32])[NH2:33])[CH2:13][N:12]2[C:11](=[O:17])[N:10]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:9]3=[O:26])=[CH:27][CH:28]=1)#[N:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 753673-Amino-3-Oxopropanoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11281440(5S,7S)-5-(4-cyanobenzyl)-3-(3,5-dichlorophenyl)-7-amino-1,3-diazabicyclo[3.3.0]octane-2,4-dione

생성물 1

HCID 11454827(5S,7S)-5-(4-Cyanobenzyl)-3-(3,5-dichlorophenyl)-7-[(2-carbamoylacetyl)amino]-1,3-diazabicyclo[3.3.0]octane-2,4-dione
수율 88%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of (5S,7S)-5-(4-cyanobenzyl)-3-(3,5-dichlorophenyl)-7-amino-1,3-diazabicyclo[3.3.0]octane-2,4-dione (200 mg), malonamic acid (59.5 mg), EDC (112 mg), HOBT (97.5 mg) and DIEA (168 μL) in THF (5 mL) was stirred overnight at room temperature. The reaction mixture was evaporated. The residue was dissolved in EtOAc and the resulting solution was washed with water, saturated aqueous NaHCO3 solution, brine, dried (Na2SO4) and concentrated to give 212 mg of the titled compound. MS (m/z) 500 (MH+).

후처리

  1. customThe reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe resulting solution was washed with water, saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0366f08fe5ef41eb97ad6555de644daf
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07375128B2

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