Acetic Acid → Cgs 22652

HRID 465610Notes

Reaction equation

HRID 465610 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([O:21]C)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(#N)C.[OH-].[Li+].C(O)(=O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 6342AcetonitrileHCID 10479691Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

Product 1

HCID 131717Cgs 22652

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3046 g of methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate, 10 l of acetonitrile and 6701 ml of 2M lithium hydroxide is stirred at room temperature overnight, and then diluted with 20 l of water. Acetic acid (1 l) is added to adjust pH to 5.5 and additional water (12 l) is added. The precipitated product is collected and resuspended in 50 l of water. The suspension is stirred, the precipitate is collected, washed with water and dried at 60°/3 mm Hg (=4.00 mbar) for 48 h. The product is recrystallized twice from ethyl acetate and once from acetonitrile to yield 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoic acid, m.p. 116.5°-118°.

Workup

  1. additionis added
  2. customThe precipitated product is collected
  3. stirringThe suspension is stirred
  4. customthe precipitate is collected
  5. washwashed with water
  6. customdried at 60°/3 mm Hg (=4.00 mbar) for 48 h
  7. customThe product is recrystallized twice from ethyl acetate and once from acetonitrile

Sources & evidence

ORD record
ord-001d16a7a7044b2a91018ec008121ab9
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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