Water → HCID 11620341, compound

HRID 1865452Notes

Reaction equation

HRID 1865452 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C@@H:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:40])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:31])[CH:24]=2)=[CH:19][CH:18]=1)[C:12]([O:14]C)=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O1CCCC1.CO.O>C(O)(=O)C>[CH2:3]([O:10][C@@H:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:40])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:31])[CH:24]=2)=[CH:19][CH:18]=1)[C:12]([OH:14])=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67304752HCID 67304752, compound

Product 1

HCID 11620341HCID 11620341, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

16 mg (0.4 mmol) of sodium hydroxide are added to a solution of 70 mg (0.42 mmol) of methyl (S)-2-benzyloxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate in 2 ml of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred overnight at ambient temperature. The reaction is halted by the addition of 2 ml of water and 0.5 ml of acetic acid, and then extraction is carried out with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated and then the residue is chromatographed on silica gel (dichloromethane/methanol 90/10). 49 mg of 2(S)-benzyloxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid are obtained in the form of an oil. Yield=72%.

Workup

  1. extractionextraction
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated
  4. customthe residue is chromatographed on silica gel (dichloromethane/methanol 90/10)

Sources & evidence

ORD record
ord-db7e3c6458bc44098c77124d166c397a
Source dataset
uspto-grants-2009_12
Patent number
US07626054B2

Reaction notes

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