Hydrochloric Acid → HCID 19348456, compound

HRID 1418151Notes

Reaction equation

HRID 1418151 reaction equation
Cl([O-])=O.[Na+].[C:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[CH:11][C:10]=1[NH:18][C:19](=[O:37])[CH2:20][CH:21]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]=[O:34])=[CH:29][C:28]=1[O:35][CH3:36])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([CH3:8])([CH3:7])[CH3:6].P([O-])(O)(O)=[O:39].[Na+].Cl>O.CS(C)=O.C(Cl)Cl.C(OCC)(=O)C>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[CH:11][C:10]=1[NH:18][C:19](=[O:37])[CH2:20][CH:21]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([OH:39])=[O:34])=[CH:29][C:28]=1[O:35][CH3:36])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([CH3:6])([CH3:7])[CH3:8]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 19348778HCID 19348778, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 19348456HCID 19348456, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 650 mg (7.19 mmol) of sodium chlorite in 7 ml of water was added dropwise over a period of 15 minutes to a solution of 1.44 g (3.18 mmol) of N-(2-t-butyl-5-carbamoylphenyl)-3-(4-formyl-2-methoxyphenyl)octanamide (prepared as described in Example 110) in a mixture of 15 ml of dimethyl sulfoxide and a 1M aqueous solution of sodium dihydrogenphosphate, and the resulting mixture was stirred for 4.5 hours. At the end of this time, the reaction mixture was acidified with 1N aqueous hydrochloric acid, and methylene chloride was added thereto to separate out crystals, which were collected by filtration. The crystals were washed with water and then with ethyl acetate to give 1.32 g (yield 89%) of the title compound as a powdery substance, melting at 204°-206° C. (from methylene chloride).

Workup

  1. additionwas added
  2. customto separate out crystals, which
  3. filtrationwere collected by filtration
  4. washThe crystals were washed with water

Sources & evidence

ORD record
ord-9fbcd761b04c4a859fa7974b31deee7a
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

Loading…