L-Serine → HCID 13316867, 화합물

HRID 2295513노트

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HRID 2295513 반응식
[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]

참가 물질

7

반응물 4

HCID 5951L-SerineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 13316857HCID 13316857, 화합물

생성물 1

HCID 13316867HCID 13316867, 화합물수율 82%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d6758c753422418d8963c94317455fc4
출처 데이터셋
uspto-grants-1984_01
특허 번호
US04425333

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