Hydrochloric Acid → HCID 70098728, compound

HRID 382178Notes

Reaction equation

HRID 382178 reaction equation
C([O:5][C:6](=[O:43])[CH2:7][C@@H:8]([C:26]1([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)[CH:30]=[CH:29][NH:28][CH2:27]1)[C:9]([NH:11]N1[C@@H](CC2C=CC=CC=2)COC1(C)C)=[O:10])(C)(C)C.[Li+].[OH-].[CH3:46][CH2:47][OH:48].Cl>C1COCC1.O>[CH2:26]([C@H:46]([NH:11][C:9](=[O:10])[C@H:8]([C:26]1([C:31]2[CH:32]=[CH:33][C:34]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:35][CH:36]=2)[CH:30]=[CH:29][NH:28][CH2:27]1)[CH2:7][C:6]([OH:5])=[O:43])[CH2:47][OH:48])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 70097970HCID 70097970, compound

Product 1

HCID 70098728HCID 70098728, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-3(S)-[3-(biphenyl-4-yl)-1H-pyrrol-3-yl]succinamic acid t-butyl ester (80 mg, 0.14 mmol) in THF (5 mL) was added 2M aqueous LiOH (5 mL). EtOH (few drops) and H2O were added until a homogeneous solution was obtained. The resultant solution was heated at 50° C. After 12 hours, the mixture was acidified with 6N HCl to pH1. After another 5.5 hours at 50° C., the mixture was partitioned between EtOAc and 1 M pH 7 phosphate buffer. The aqueousueous phase was separated and extracted with EtOAc two times. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to a residue which, upon trituration with CH2Cl2/hex, provided 32 mg (49%) of pure N-(1(S)-benzyl-2-hydroxyethyl)-3(S)-[3-(biphenyl-4-yl)-1H-pyrrol-3-yl]succinamic acid as a white solid, mp 151-4° C.

Workup

  1. customwas obtained
  2. waitAfter another 5.5 hours at 50° C.
  3. customthe mixture was partitioned between EtOAc and 1 M pH 7 phosphate buffer
  4. customThe aqueousueous phase was separated
  5. extractionextracted with EtOAc two times
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to a residue which, upon trituration with CH2Cl2/hex

Sources & evidence

ORD record
ord-3924923abf3648c3bbef8d876cfd8046
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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