Hydrochloric Acid → HCID 131724985, compound

HRID 1071190Notes

Reaction equation

HRID 1071190 reaction equation
[ClH:1].S(=O)(=O)(O)O.[CH2:7]([C@@H:9]([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([NH2:23])[CH:19]=2)[O:14]1)[C:10]([OH:12])=[O:11])[CH3:8]>C(O)C>[ClH:1].[CH2:7]([C@@H:9]([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([NH2:23])[CH:19]=2)[O:14]1)[C:10]([OH:12])=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131724986HCID 131724986, compound2×

Product 1

HCID 131724985HCID 131724985, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

A 2-L three-neck round-bottom flask equipped with a condenser and a stirrer was charged with ethyl (2S)-(6-aminochroman-2-yl)acetic acid, bisulfate salt in 500 mL of toluene (Example 8). The reaction was cooled to about 10° C., and 55 mL of 5.8 M hydrochloric acid in absolute ethanol was added to the well-stirred solution. The resulting suspension was stirred for 17 h, then the crystals were allowed to settle. The white crystals were filtered, washed with 250 mL of toluene, and dried at 60° C. under reduced pressure to afford 75 g of ethyl (2S)-(6-aminochroman-2-yl)acetic acid, hydrochloride salt (92% with respect to (2S)-(6-acetamidochroman-2-yl)acetic acid, D-alaninol salt from Example 7). The product was >99% pure and the enantiomeric excess was >99.5% by chromatography and NMR.

Workup

  1. customA 2-L three-neck round-bottom flask equipped with a condenser and a stirrer
  2. filtrationThe white crystals were filtered
  3. washwashed with 250 mL of toluene
  4. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-886e20dee17c4ab09a3ad276b1b95559
Source dataset
uspto-grants-2005_06
Patent number
US06903227B2

Reaction notes

Loading…