Hydrochloric Acid → HCID 67102521, compound

HRID 2080908Notes

Reaction equation

HRID 2080908 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:31])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:18][CH:19]=[CH:20][CH2:21][CH:22]([OH:30])[C:23]1([CH2:27][CH2:28][CH3:29])[CH2:26][CH2:25][CH2:24]1)[S:14]([CH3:17])(=[O:16])=[O:15])C.Cl>O.C1COCC1>[OH:30][CH:22]([C:23]1([CH2:27][CH2:28][CH3:29])[CH2:26][CH2:25][CH2:24]1)[CH2:21][CH:20]=[CH:19][CH2:18][N:13]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:31])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67101396HCID 67101396, compound

Product 1

HCID 67102521HCID 67102521, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.50 mL of a 0.5N solution in H2O, 0.122 mmol) was added to a solution of the ester 11 (45 mg, 0.122 mmol) in THF (1.0 mL) at 23° C. The reaction mixture was stirred for 16 h, acidified with 1 N HCl and extracted with EtOAc. The organic portion was washed with brine (2×), dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 100% EtOAc) gave 36.2 mg (72%) of the free acid 12 as a light yellow, viscous oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic portion was washed with brine (2×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7b201c1323f4b70a59230ea369ea33a
Source dataset
uspto-grants-2011_04
Patent number
US07932420B2

Reaction notes

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