Citric Acid → HCID 66870865, 화합물

HRID 579669노트

반응식

HRID 579669 반응식
C([O:3][C:4]([C:6]12[CH2:24][CH:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:14](=[O:34])[N:13]1[CH:9]([CH2:10][CH:11]([O:35][C:36]3[C:45]4[C:40](=[C:41]([CH3:48])[C:42]([O:46][CH3:47])=[CH:43][CH:44]=4)[N:39]=[C:38]([C:49]4[S:50][CH:51]=[C:52]([CH:54]([CH3:56])[CH3:55])[N:53]=4)[CH:37]=3)[CH2:12]1)[C:8](=[O:57])[NH:7]2)=[O:5])C.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[CH:54]([C:52]1[N:53]=[C:49]([C:38]2[CH:37]=[C:36]([O:35][CH:11]3[CH2:10][CH:9]4[N:13]([C:14](=[O:34])[N:15]([CH2:25][C:26]5[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=5)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH:23]5[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]4=[O:57])[CH2:24]5)[CH2:12]3)[C:45]3[C:40](=[C:41]([CH3:48])[C:42]([O:46][CH3:47])=[CH:43][CH:44]=3)[N:39]=2)[S:50][CH:51]=1)([CH3:56])[CH3:55]

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 66870831HCID 66870831, 화합물

생성물 1

HCID 66870865HCID 66870865, 화합물수율 60%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

Ethyl ester 137 (366 mg, 0.460 mmol) was dissolved in THF/MeOH/H2O 2:1:1 (30 mL) and 1M LiOH (4.6 mL, 4.40 mmol) was added dropwise at room temperature during 5 minutes after which the solution was stirred overnight. The mixture was acidified to pH 3-4 by addition of solid citric acid and the organic solvents were evaporated. The water phase was diluted with brine (50 mL) and was then extracted trice with DCM. The combined organic phase was washed twice with brine and was thereafter dried, filtered and concentrated. The crude was then purified by flash column chromatography (ethyl acetate/methanol 7:1) to give the title compound (212 mg, 60%). (M+H)+ calcd: 768.3; found: 768.7.

후처리

  1. customthe organic solvents were evaporated
  2. additionThe water phase was diluted with brine (50 mL)
  3. extractionwas then extracted trice with DCM
  4. washThe combined organic phase was washed twice with brine
  5. customwas thereafter dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was then purified by flash column chromatography (ethyl acetate/methanol 7:1)

출처 및 근거

ORD 기록
ord-322150d620f24291a7a1b3e309144660
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040562B2

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