Hydrochloric Acid → HCID 9845429, compound

HRID 369373Notes

Reaction equation

HRID 369373 reaction equation
[OH:1][CH:2]([C:23]1[CH:28]=[CH:27][C:26]([O-:29])=[C:25]([CH2:30][OH:31])[CH:24]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O-:22])=[O:21])=[CH:10][CH:11]=2)[CH2:6]1.[Na+].[Na+].Cl>O>[OH:1][CH:2]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([CH2:30][OH:31])[CH:24]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:10][CH:11]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21971939HCID 21971939, compound2×

Product 1

HCID 9845429HCID 9845429, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Disodium 6-[(2S)-2-[[(2RS)-2-hydroxy-2-(3-hydroxymethyl-4-oxidophenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yl]hexanoate (Compound 11) (20 mg) was dissolved in water (192 μl), and 1 N hydrochloric acid (77 μl) was added to the solution under ice-cooling with stirring. After reaction for 2 hours, the reaction mixture was concentrated in vacuo, and methanol was added to the residue. The insoluble material was filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by medium pressure liquid column chromatography on octadecyl silica gel (eluent: water/acetonitrile=2/1) gave 6-[(2S)-2-[[(2RS)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yl]hexanoic acid (Compound 12) (12 mg) as an amorphous.

Workup

  1. temperaturecooling
  2. customAfter reaction for 2 hours
  3. concentrationthe reaction mixture was concentrated in vacuo, and methanol
  4. additionwas added to the residue
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customPurification of the residue by medium pressure liquid column chromatography on octadecyl silica gel (eluent: water/acetonitrile=2/1)

Sources & evidence

ORD record
ord-6ce3fbca8b7e46cdb356640dfec50944
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

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