Hydrochloric Acid → HCID 86585191, compound

HRID 844348Notes

Reaction equation

HRID 844348 reaction equation
C([O:4][C:5](=[O:44])[CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@@H:12]1[C@H:16]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:15][C@H:14]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[C@H:13]1[CH2:31][O:32][C:33](=[S:43])[NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=1)C=C.[OH-].[Li+].Cl>C1COCC1.O>[Cl:42][C:38]1[CH:37]=[C:36]([CH:41]=[CH:40][CH:39]=1)[CH2:35][NH:34][C:33]([O:32][CH2:31][C@@H:13]1[C@@H:14]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH2:15][C@@H:16]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C@H:12]1[CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][C:5]([OH:44])=[O:4])=[S:43]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86585192HCID 86585192, compound

Product 1

HCID 86585191HCID 86585191, compoundYield 72.6%

Reagents, catalysts & solvents 1

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

Procedure

A solution of ester 6 (614 mg, 0.97 mmol) and lithium hydroxide (62 mg, 1.5 mmol) in THF/H2O (1:1, 20 mL) was stirred at 23° C. for 72 h. The mixture was acidified with 1N HCl and extracted with EtOAc. The organic portion was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give 430 mg of the above titled compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic portion was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d13524edc5d445cbc7af3c1c32dc056
Source dataset
uspto-grants-2002_04
Patent number
US06380251B1

Reaction notes

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