Thioglycolic Acid → (S)-3-[(S)-2-(4-Hydroxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-((S)-1-phenyl-propylamino)-propionic acid methyl ester

HRID 879698ノート

反応式

HRID 879698 の反応式
[CH3:1][O:2][C:3](=[O:48])[C@@H:4]([N:26](S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[C@H:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:28][CH3:29])[CH2:5][C:6]1[CH:25]=[CH:24][C:9]2[O:10][C@@H:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C(=O)C)=[CH:16][CH:15]=3)[CH2:12][O:13][C:8]=2[CH:7]=1.SCC(O)=O.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:48])[C@@H:4]([NH:26][C@H:27]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:28][CH3:29])[CH2:5][C:6]1[CH:25]=[CH:24][C:9]2[O:10][C@@H:11]([C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)[CH2:12][O:13][C:8]=2[CH:7]=1

参加物

5

反応物 3

HCID 1133Thioglycolic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58327168(S)-3-[(S)-2-(4-Acetoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-[(4-nitro-benzenesulfonyl)-((S)-1-phenyl-propyl)-amino]-propionic acid methyl ester

生成物 1

HCID 58327220(S)-3-[(S)-2-(4-Hydroxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-((S)-1-phenyl-propylamino)-propionic acid methyl ester収率 78.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(S)-3-[(S)-2-(4-Acetoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-[(4-nitro-benzenesulfonyl)-((S)-1-phenyl-propyl)-amino]-propionic acid methyl ester (230 mg) was dissolved in 3 mL dry DMF, then, mercaptoacetic acid and DBU were added at rt. The reaction stirred over night, and was partitioned between saturated aqueous NaHCO3 and diethyl ether. The organic layer was washed successively with aqueous NaHCO3, water, and brine, then was dried with Na2SO4 and evaporated. The residue was purified by silica gel flash chromatography (9:1 to 8:2 hexanes/EtOAc) to give 120 mg desired product. LCMS (m/z): 449.

後処理

  1. customwas partitioned between saturated aqueous NaHCO3 and diethyl ether
  2. washThe organic layer was washed successively with aqueous NaHCO3, water, and brine
  3. dry with materialwas dried with Na2SO4
  4. customevaporated
  5. customThe residue was purified by silica gel flash chromatography (9:1 to 8:2 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-3335e5537e8b493ea6d1a4457409353a
出典データセット
uspto-grants-2015_03
特許番号
US08987295B2

反応ノート

読み込み中…