Hydrochloric Acid → HCID 51671084, compound

HRID 1983999Notes

Reaction equation

HRID 1983999 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:10]([CH2:17][C:18]([OH:20])=[O:19])[CH2:9]1)=O)(C)(C)C.Cl.[CH3:22]O>C(OCC)C>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:10]([CH2:17][C:18]([O:20][CH3:22])=[O:19])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68853807HCID 68853807, compound

Product 1

HCID 51671084HCID 51671084, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

(+)-(S)-(1-tert-Butoxycarbonyl-2,3-dihydro-1H-indol-3-yl)acetic acid (14.2 g, 0.05 mol) was dissolved in methanol (600 mL), cooled (5° C.) and a saturated solution of HCl in diethyl ether (150 mL) was added. The resulting mixture was stirred at room temperature for 16 h, concentrated in vacuo to about 50 mL and poured onto an ice/water mixture. The aqueous phase was extracted with ethyl acetate and diethyl ether, and the combined organic phases were washed with aqueous ammonia and brine. The organic phase was dried and concentrated in vacuo to give the title compound (9.8 g, 100%).

Workup

  1. concentrationconcentrated in vacuo to about 50 mL
  2. additionpoured onto an ice/water mixture
  3. extractionThe aqueous phase was extracted with ethyl acetate and diethyl ether
  4. washthe combined organic phases were washed with aqueous ammonia and brine
  5. customThe organic phase was dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74831fae87d74188b29507dba9a7ed51
Source dataset
uspto-grants-2009_06
Patent number
US07544685B2

Reaction notes

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