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Imidazole → HCID 22876421, 화합물

HRID 2394100
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HRID 2394100 반응식
[C:1]([NH:8][C@@H:9]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@@H:10]([OH:35])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:26][C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:34])(=[O:25])=[O:24])=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:43]([Si:47]([CH3:50])([CH3:49])Cl)([CH3:46])([CH3:45])[CH3:44].N1C=CN=C1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CO.C1COCC1.O.CCCCCC.C(OCC)(=O)C>[C:1]([NH:8][C@@H:9]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@@H:10]([O:35][Si:47]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:50])[CH3:49])[CH2:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:26][C:27]2[C:28]([Cl:34])=[CH:29][CH:30]=[CH:31][C:32]=2[Cl:33])(=[O:25])=[O:24])=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

10

반응물 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 22876407HCID 22876407, 화합물

생성물 1

HCID 22876421HCID 22876421, 화합물

시약·촉매·용매 5

HCID 887Methanol용매
HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 8028Tetrahydrofuran용매
HCID 21226206Ethyl acetate hexane용매

실험 절차

In analogy with Example 5f), 5.0 g (7.85 mmol) of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-{[p-(2,6-dichlorobenzylsulfonyl)phenyl]methyl}hexanoic acid in 74 ml of DMF are silylated with 5.4 g (36.1 mmol) of tert-butyldimethylchlorosilane and 4.4 g (64.4 mmol) of imidazole. Hydrolysis of the silyl ester function with 6.5 g of potassium carbonate in 85 ml of methanol, 22 ml of THF and 22 ml of water yields the title compound after column chromatography (SiO2, hexane/ethyl acetate, 1:1) and stirring-up with DIPE: TLC Rf (C)=0.5; tRet (II)=21.0 min.

출처 및 근거

ORD 기록
ord-f2b425ab1e664e94ba37556df44eea07
출처 데이터셋
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05807891

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