Hydrochloric Acid → HCID 66644546, compound

HRID 576885Notes

Reaction equation

HRID 576885 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([N:27]([CH3:44])[NH:28][C:29](=[O:43])[CH2:30][CH2:31][NH:32][C:33]([NH:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[C:17]([O:19]CC2C=CC=CC=2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]([N:27]([CH3:44])[NH:28][C:29](=[O:43])[CH2:30][CH2:31][NH:32][C:33]([NH:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 86663950HCID 86663950, compound

Product 1

HCID 66644546HCID 66644546, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-benzyl 3-(4-(benzyloxy)phenyl)-2-(2-(3-(3-benzylureido)propanoyl)-1-methylhydrazinyl)propanoate (Compound XVII-1) 149 mg (0.25 mmol) in tetrahydrofuran:methanol=1:1.5 1.5 ml, a solution of lithium hydroxide monohydrate 16 mg in water 0.3 ml was added and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was cooled to 0° C. and 1N HCl aq. 10 ml was added and the mixture was extracted with ethyl acetate 20 ml. The organic phase was washed with water 20 ml and brine 20 ml and dried over magnesium sulfate and filtered. The mother solution was concentrated in vacuo to obtain the title compound. The residue was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionthe mixture was extracted with ethyl acetate 20 ml
  3. washThe organic phase was washed with water 20 ml and brine 20 ml
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe mother solution was concentrated in vacuo

Sources & evidence

ORD record
ord-76ef4c7783254959b6bdbc58b026f2bf
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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