Hydrochloric Acid → HCID 14372572, compound

HRID 620276Notes

Reaction equation

HRID 620276 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][CH2:22][S:23][CH3:24])[CH:3]=1.Cl.I([O-])(=O)(=O)=[O:27].[Na+].[OH-].[Na+]>O>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][CH2:22][S:23]([CH3:24])=[O:27])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14372571HCID 14372571, compoundHCID 23667635Sodium periodate

Product 1

HCID 14372572HCID 14372572, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of product from Example 49 (1.496 g, 4 mmoles) in 2N hydrochloric acid (5.0 ml, 10 mmoles) and water (20 ml) was added sodium periodate (856 mg. 4.0 mmoles) and the mixture stirred for 2.5 hours. It was then basified with 4N sodium hydroxide (3 ml) and extracted with methylene chloride (3×30 ml). The extracted was concentrated in vacuo and the residue flash-chromatographed on deactivated silica column using methylene chloride:methanol:ammonia (100:3.5:0.5) solvent system. The appropriate fractions were combined and concentrated to give a yellow oil which crystallized from methylene chloride-ether to give 770 mg of the title product as a light yellow solid, mp. 116°-117° C.

Workup

  1. extractionextracted with methylene chloride (3×30 ml)
  2. concentrationThe extracted was concentrated in vacuo
  3. customthe residue flash-chromatographed on deactivated silica column
  4. concentrationconcentrated
  5. customto give a yellow oil which
  6. customcrystallized from methylene chloride-ether

Sources & evidence

ORD record
ord-f2c9656dd14b499c9dfa872260be7e06
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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