Hydrochloric Acid → HCID 57500409, compound

HRID 2273552Notes

Reaction equation

HRID 2273552 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[N:22]3[C:17]([C:18]([OH:23])=[CH:19][CH:20]=[CH:21]3)=[C:16]([O:24][CH3:25])[C:15]=2[CH3:26])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47]I.Cl>O1CCCC1>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[N:22]3[C:17]([C:18]([O:23][CH2:47][CH2:46][O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][I:27])=[CH:19][CH:20]=[CH:21]3)=[C:16]([O:24][CH3:25])[C:15]=2[CH3:26])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 57500344HCID 57500344, compoundHCID 57500345HCID 57500345, compound

Product 1

HCID 57500409HCID 57500409, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

12 ml (6.0 mmol) of potassium hexamethyldisilylamide (0.5 M solution in toluene) at −20° C. under nitrogen is added, dropwise, to the solution of 2.0 g (5.64 mmol) of methyl 2-amino-5-[(8-hydroxy-1-methoxy-2-methyl-indolizin-3-yl)carbonyl]benzoate (described in stage F of Example 1) in 56 ml of tetrahydrofuran. The formation of a red precipitate is observed. The mixture is allowed to return to ambient temperature and 18.5 g (33.9 mmol) of 1,20-diiodo-3,6,9,12,15,18-hexaoxaicosane are added (Example R1). The solution is stirred at ambient temperature for 18 hours. The reaction medium is poured into a solution of hydrochloric acid (1 M) and the mixture is extracted with an ethyl acetate/tetrahydrofuran mixture. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue obtained is purified by flash chromatography on silica gel (gradient of dichloromethane/methanol: 100/0 to 90/10). 2.3 g (53%) of a yellow oil are obtained.

Workup

  1. customto return to ambient temperature
  2. extractionthe mixture is extracted with an ethyl acetate/tetrahydrofuran mixture
  3. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by flash chromatography on silica gel (gradient of dichloromethane/methanol: 100/0 to 90/10)

Sources & evidence

ORD record
ord-fb2b26a5d16f4d47843061eeb87bfdeb
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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