Hydrochloric Acid → HCID 54087286, compound

HRID 442794Notes

Reaction equation

HRID 442794 reaction equation
[CH:1]1[C:14]2[CH:13]([CH2:15][C:16]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]([O:31]C)=[O:30])=[C:25]([O:33][CH3:34])[CH:24]=4)[NH:20]C(=O)N[C:17]3=[O:22])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[OH-:36].[Na+]>>[NH2:20][C:16]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([OH:31])=[O:30])=[C:25]([O:33][CH3:34])[CH:24]=1)([CH2:15][CH:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:17]([OH:36])=[O:22]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54308334HCID 54308334, compound

Product 1

HCID 54087286HCID 54087286, compound

Procedure

A suspension of 5-(9H-xanthen-9-ylmethyl)-5-(3-methoxy-4-methoxycarbonylphenyl)hydantoin (1.04 g, 2.27 mmol) in aqueous sodium hydroxide (2M, 6.8 ml) was heated at 120° C. in a teflon lined stainless steel sealed tube for 3 days with stirring. After cooling, aqueous hydrochloric acid (5M, 3 ml) was added followed by purification on ion exchange (Dowex50×8-100 resin). The column was eluted sequentially with water, water-tetrahydrofuran (1:1), water and 10% pyridine in water. Fractions collected after the pyridine-water elution were combined, evaporated to dryness, redissolved in water and freeze-dried to give 2-amino-2-(4-carboxy-3-methoxyphenyl)-3-(9H-xanthen-9-yl)propanoic acid as a white powder.

Workup

  1. customfor 3 days
  2. temperatureAfter cooling
  3. customfollowed by purification on ion exchange (Dowex50×8-100 resin)
  4. washThe column was eluted sequentially with water, water-tetrahydrofuran (1:1), water and 10% pyridine in water
  5. customFractions collected
  6. washafter the pyridine-water elution
  7. customevaporated to dryness
  8. dissolutionredissolved in water
  9. customfreeze-dried

Sources & evidence

ORD record
ord-2ad291c794c949ba86196cd8205269b3
Source dataset
uspto-grants-1999_04
Patent number
US05891899

Reaction notes

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