Sodium Carbonate → HCID 20577182、化合物

HRID 1266243ノート

反応式

HRID 1266243 の反応式
Cl.[NH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=2)[CH:10]=[CH:11][CH:12]=1)=[O:5].C(=O)([O-])[O-].[Na+].[Na+].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[Cl:55][C:56]1[CH:57]=[C:58]([CH:64]=[CH:65][CH:66]=1)[C@@H:59]([OH:63])[C:60](O)=[O:61]>C(OCC)(=O)C>[Cl:55][C:56]1[CH:57]=[C:58]([C@H:59]([OH:63])[C:60]([NH:2][CH2:3][C:4]([NH:6][C:7]2[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=3)[CH:10]=[CH:11][CH:12]=2)=[O:5])=[O:61])[CH:64]=[CH:65][CH:66]=1

参加物

7

反応物 5

HCID 10340Sodium CarbonateHCID 10868DicyclohexylcarbodiimideHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 69712085Methyl 3'-[(aminoacetyl)amino][1,1'-biphenyl]-3-carboxylate hydrochloride

生成物 1

HCID 20577182HCID 20577182、化合物収率 426.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
10 °C

実験手順

A suspension of methyl 3′-[(aminoacetyl)amino][1,1′-biphenyl]-3-carboxylate hydrochloride (50 g) in ethyl acetate (350 ml) is treated with 1 M aqueous sodium carbonate (250 ml) at room temperature. The lower aqueous phase is discarded, 1-hydroxybenzotriazole hydrate (10 g) and then dicyclohexylcarbodiimide (30.6 g) is added to the organic phase and the mixture is cooled to approximately 10° C. This mixture is treated with a solution of (R)-3-chloromandelic acid (5.8 g) in ethyl acetate (40 ml) over approximately 1 hour. The mixture is stirred for several hours and filtered. The filtrate is washed with 6% w/w aqueous sodium bicarbonate and water, and the organic phase is concentrated to low volume. Isopropanol is added and the organic solution is further concentrated to low volume. The organic solution is warmed to 70° C., treated with water, cooled to room temperature and the mixture is filtered to give the title product (60 g).

後処理

  1. filtrationfiltered
  2. washThe filtrate is washed with 6% w/w aqueous sodium bicarbonate and water
  3. concentrationthe organic phase is concentrated to low volume
  4. additionIsopropanol is added
  5. concentrationthe organic solution is further concentrated to low volume
  6. temperatureThe organic solution is warmed to 70° C.
  7. additiontreated with water
  8. temperaturecooled to room temperature
  9. filtrationthe mixture is filtered

出典と根拠

ORDレコード
ord-b40b4e4c778644bb8dd9ed100cf4d927
出典データセット
uspto-grants-2003_04
特許番号
US06548523B2

反応ノート

読み込み中…