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Acetic Acid → 3-(4-thiazolyl)-L-alanine diphenylmethylester p-toluenesulfonate

HRID 429756
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인쇄 미리보기

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HRID 429756 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[S:12]1[CH:16]=[C:15]([CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])[N:14]=[CH:13]1.C1COCC1.[C:28]1([C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N+]=[N-])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(=O)C>C(O)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[C:28]1([CH:34]([O:21][C:20](=[O:22])[C@H:18]([CH2:17][C:15]2[N:14]=[CH:13][S:12][CH:16]=2)[NH2:19])[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 612301,1'-(Diazomethylene)bis(benzene)2회HCID 867576003-(4-thiazolyl)-L-alanine p-toluenesulfonate

생성물 1

HCID 207060783-(4-thiazolyl)-L-alanine diphenylmethylester p-toluenesulfonate수율 96.1%

시약·촉매·용매 1

HCID 702
Ethanol
용매

실험 절차

To a solution of 38.85 g of the compound (43) (112.8 mmol) in ethanol (200 ml)-THF (600 ml) was added diphenyldiazomethane (39 g, 201 mmol) little, by little over 30 min. at room temperature with stirring. After the reaction mixture was stirred for 1 h at room temperature, to the mixture was added diphenyldiazomethane (10 g, 51.5 mmol) and the resulting mixture was stirred for 1 h. To the reaction mixture was added acetic acid (0.1 ml) for quenching the excess reagent and the mixture was concentrated in vacuo. The residue (92 g) was crystallized by adding ether (1 L) to give 49.05 g (96.1%) of the compound (44).

후처리

  1. stirringAfter the reaction mixture was stirred for 1 h at room temperature, to the mixture
  2. stirringthe resulting mixture was stirred for 1 h
  3. customfor quenching the excess reagent
  4. concentrationthe mixture was concentrated in vacuo
  5. customThe residue (92 g) was crystallized
  6. additionby adding ether (1 L)

출처 및 근거

ORD 기록
ord-c8878d1f1d7446cd84b6489225952cd9
출처 데이터셋
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06319902B1

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