Hydrochloric Acid → HCID 58826644, compound

HRID 1012315Notes

Reaction equation

HRID 1012315 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:24]=[CH:23][C:22]([C:25](Cl)=[O:26])=[CH:21][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:28][C@@H:29]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31].Cl>C(Cl)(Cl)Cl>[CH:1]1([C:7]2[C:8]3[CH:24]=[CH:23][C:22]([C:25]([NH:28][C@@H:29]([CH2:34][C:35]4[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=4)[C:30]([O:32][CH3:33])=[O:31])=[O:26])=[CH:21][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70652Tyrosine Methyl EsterHCID 23152653HCID 23152653, compound

Product 1

HCID 58826644HCID 58826644, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl chloride (100 mg, 0.26 mmol) in chloroform (2 ml) was added methyl (S)-2-amino-3-(4-hydroxyphenyl)propionate (154 mg, 0.78 mmol). The mixture was stirred at room temperature for 12 hr, 1N hydrochloric acid was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. After filtration and concentration, diethyl ether was added to the obtained residue, and the precipitated solid was collected by filtration. The solid was washed with diethyl ether to give methyl (S)-2-[(12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-3-(4-hydroxyphenyl)propionate (102 mg, yield 82%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was successively washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration and concentration, diethyl ether
  5. additionwas added to the obtained residue
  6. filtrationthe precipitated solid was collected by filtration
  7. washThe solid was washed with diethyl ether

Sources & evidence

ORD record
ord-4751dc6313164ca6af697e054ef117fd
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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