L-Serine → HCID 13316867、化合物

HRID 2295513ノート

反応式

HRID 2295513 の反応式
[C:1]([S:4][CH2:5][CH2:6][C:7]([N:9]1[C@H:13]([C:14]([OH:16])=O)[CH2:12][S:11][C@@H:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:8])(=[O:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.[NH2:39][C@H:40]([C:43]([OH:45])=[O:44])[CH2:41][OH:42]>C(N(CC)CC)C.C1COCC1>[C:1]([S:4][CH2:5][CH2:6][C:7]([N:9]1[C@H:13]([C:14]([NH:39][C@H:40]([C:43]([OH:45])=[O:44])[CH2:41][OH:42])=[O:16])[CH2:12][S:11][C@@H:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:8])(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 5951L-SerineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 13316857HCID 13316857、化合物

生成物 1

HCID 13316867HCID 13316867、化合物収率 82%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

The suspension of mixed anhydride is prepared by using 3.55 g of (2R,4R)-3-(S-acetyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid, 1.0 g of N-methylmorpholine, 1.4 g of isobutyl chlorocarbonate and 60 ml of THF in the same manner as Example 1. To the suspension 20 ml of the aqueous solution of 2.1 g of L-serine and 2.0 g of triethylamine is added. The mixture is stirred under ice-cooling for 30 minutes and at room temperature for an additional 1 hour. After removing THF in vacuo, it is acidified with N--HCl, and extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue is crystallized from benzene to give 3.6 g (82%) of the titled compound.

後処理

  1. customis prepared
  2. customAfter removing THF in vacuo, it
  3. extractionHCl, and extracted with ethyl acetate
  4. washThe organic layer is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is crystallized from benzene

出典と根拠

ORDレコード
ord-d6758c753422418d8963c94317455fc4
出典データセット
uspto-grants-1984_01
特許番号
US04425333

反応ノート

読み込み中…