Hydrochloric Acid → HCID 56952891, compound

HRID 879254Notes

Reaction equation

HRID 879254 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][N:7]([CH3:68])[C@H:8]([C:12]([NH:14][C@H:15]([C:19]([N:21]([C@@H:23]([C@@H:64]([CH3:67])[CH2:65][CH3:66])[C@H:24]([O:62][CH3:63])[CH2:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C@H:33]([O:60][CH3:61])[C@@H:34]([CH3:59])[C:35]([NH:37][C@@H:38]([CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]([O:50]C)=[O:49])=[CH:44][CH:43]=1)=[O:36])=[O:27])[CH3:22])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH:9]([CH3:11])[CH3:10])([OH:3])=[O:2].[OH-].[Li+].Cl>C1COCC1.O>[C:1]([CH2:4][CH2:5][CH2:6][N:7]([CH3:68])[C@H:8]([C:12]([NH:14][C@H:15]([C:19]([N:21]([C@@H:23]([C@@H:64]([CH3:67])[CH2:65][CH3:66])[C@H:24]([O:62][CH3:63])[CH2:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C@H:33]([O:60][CH3:61])[C@@H:34]([CH3:59])[C:35]([NH:37][C@@H:38]([CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH2:39][O:40][CH2:41][C:42]1[CH:43]=[CH:44][C:45]([C:48]([OH:50])=[O:49])=[CH:46][CH:47]=1)=[O:36])=[O:27])[CH3:22])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH:9]([CH3:11])[CH3:10])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 56952799HCID 56952799, compound

Product 1

HCID 56952891HCID 56952891, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

7.5 mg (8 μmol) of N-(3-carboxypropyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-3-{[(2S)-1-{[4-(methoxycarbonyl)benzyl]oxy}-3-phenylpropane-2-yl]amino}-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide (example 26) were dissolved in 0.25 ml of THF/water (1:1). 0.8 mg (32 μmol) of lithium hydroxide were added and the batch stirred for 3 hours at RT. Then, the reaction composition was acidized with 1 N hydrochloric acid and extracted three times with 5 ml of ethyl acetate each. The organic phases were dried over magnesium sulphate and evaporated in a vacuum. Following lyophilization from dioxane, the yield was 2.3 mg (71% purity, 22% o. th.) of the title compound in the form of a white solid substance.

Workup

  1. extractionextracted three times with 5 ml of ethyl acetate each
  2. dry with materialThe organic phases were dried over magnesium sulphate
  3. customevaporated in a vacuum

Sources & evidence

ORD record
ord-9fa01ba863a84cb7842cfeacdaf47228
Source dataset
uspto-grants-2015_03
Patent number
US08987209B2

Reaction notes

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