Sodium Hydroxide → methyl (R)-2-(3-1H-imidazol-4-ylpropionylamino)-3-(4-methoxyphenyl)propanoate

HRID 540379노트

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HRID 540379 반응식
CCN(C(C)C)C(C)C.Cl.[CH2:11]([C:18]([OH:20])=O)[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:43][C@H:44]([CH2:49][C:50]1[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=1)[C:45]([O:47][CH3:48])=[O:46].[OH-].[Na+]>CN(C=O)C>[NH:15]1[CH:14]=[C:13]([CH2:12][CH2:11][C:18]([NH:43][C@H:44]([CH2:49][C:50]2[CH:51]=[CH:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=2)[C:45]([O:47][CH3:48])=[O:46])=[O:20])[N:17]=[CH:16]1

참가 물질

7

반응물 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11241250(R)-Methyl 2-amino-3-(4-methoxyphenyl)propanoateHCID 178479756HCID 178479756, 화합물

생성물 1

HCID 178501382methyl (R)-2-(3-1H-imidazol-4-ylpropionylamino)-3-(4-methoxyphenyl)propanoate수율 49%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

35.5 ml of DIEA are added to a solution containing 13.2 g (74.7 mmol) of desamino-histidine hydrochloride and 24 g (74.7 mmol) of TBTU in 100 ml of DMF. After stirring for 15 minutes at ambient temperature, 14.2 g (67.9 mmol) of methyl (R)-2-amino-3-(4-methoxyphenyl)-propanoate in 150 ml of DMF are added. The reaction medium is left to stir for 16 hours and then basified to pH=8-9 by introducing 1N sodium hydroxide and a saturated solution of sodium hydrogen carbonate, followed by extraction with dichloromethane. The organic phase is dried over sodium sulphate, filtered and evaporated. The crude product obtained is purified by silica gel chromatography (eluent 85/15 dichloromethane/methanol). 11.0 g in the form of an orange oil are obtained with a yield of 49%.

후처리

  1. waitThe reaction medium is left
  2. stirringto stir for 16 hours
  3. extractiona saturated solution of sodium hydrogen carbonate, followed by extraction with dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-cad5a82c6e154366b59be598db2208ee
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871187B2

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