Dichloromethane → HCID 14208554, compound

HRID 845327Notes

Reaction equation

HRID 845327 reaction equation
[CH3:1][C:2]([CH3:29])([O:4][C:5]([NH:7][C@H:8]([C:17]([NH:19][C@@H:20]([C:25]([O:27]C)=[O:26])[CH2:21][CH2:22][S:23][CH3:24])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:6])[CH3:3].[OH-].[K+].OS([O-])(=O)=O.[K+].C(Cl)Cl>O1CCCC1.O>[CH3:3][C:2]([CH3:29])([O:4][C:5]([NH:7][C@H:8]([C:17]([NH:19][C@@H:20]([C:25]([OH:27])=[O:26])[CH2:21][CH2:22][S:23][CH3:24])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:6])[CH3:1]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 516920Potassium bisulfateHCID 14208549HCID 14208549, compound

Product 1

HCID 14208554HCID 14208554, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title product of Example 1 (25.0 g, 58.6 mmol) dissolved in 150 ml of tetrahydrofuran (THF) was combined with a solution of potassium hydroxide (KOH, 7.7 g, 0.12 mmol) dissolved in 375 ml of water. After this reaction was stirred for 4 h, it was poured into a mixture of 2.5N KHSO4 (400 ml) and CH2Cl2 (500 ml). The organic layer was separated and the aqueous (pH2) was extracted 3×100 ml of CH2Cl2. The combined organics were washed with 150 ml of brine, dried over Na2SO4, and stripped of all solvent under reduced pressure. The residue, after in vacuo drying, yielded 25 g of the title product as a white powder. This material was used without further purification.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous (pH2) was extracted 3×100 ml of CH2Cl2
  3. washThe combined organics were washed with 150 ml of brine
  4. dry with materialdried over Na2SO4
  5. customThe residue, after in vacuo drying

Sources & evidence

ORD record
ord-d5a9b3b4bae54416ae130b85d5ffa532
Source dataset
uspto-grants-1988_07
Patent number
US04757153

Reaction notes

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