L-Alanine → HCID 68428367, 화합물

HRID 642285노트

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HRID 642285 반응식
C(O[C:4]([C:6]1[N:11]=[C:10]([CH3:12])[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])C.[NH2:23][C@H:24]([C:26]([OH:28])=[O:27])[CH3:25]>C[O-].[Na+].CO>[OH:22][C:7]1[C:8]2[S:15][C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:13][C:9]=2[C:10]([CH3:12])=[N:11][C:6]=1[C:4]([NH:23][CH:24]([CH3:25])[C:26]([OH:28])=[O:27])=[O:5]

참가 물질

4

반응물 2

HCID 5950L-AlanineHCID 68426288HCID 68426288, 화합물

생성물 1

HCID 68428367HCID 68428367, 화합물수율 38.5%

시약·촉매·용매 1

HCID 23694274Sodium methanolate methanol용매

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온도
120 °C

실험 절차

A mixture of 7-hydroxy-4-methyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (50 mg, 0.16 mmol) and L-alanine (146 mg, 1.63 mmol) in 0.5 M sodium methoxide/methanol (2.6 mL) was heated at 120° C. in a microwave vessel for 3 h before it was cooled to room temperature and concentrated in vacuo. Water was added to the residue and extracted four times with dichloromethane until no UV spot in the dichloromethane layer. The remaining aqueous layer was acidified to pH=3 with 1N HCl (2 mL). The suspension was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to give the title compound as a white solid (22 mg): 1H NMR (DMSO-d6, 200 MHz): δ=12.98 (br s, 1H), 9.06 (d, J=7.4 Hz, 1H), 8.15 (m, 2H), 7.61 (m, 3H), 4.54 (m, 1H), 2.88 (s, 3H), 1.49 (d, J=7.4 Hz, 3H); MS: (+) m/z 358.04 (M+1).

후처리

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionWater was added to the residue
  4. extractionextracted four times with dichloromethane until no UV spot in the dichloromethane layer
  5. extractionThe suspension was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-17aeb23ba8774985a75257876539bcb1
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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