Hydrochloric Acid → 2-Amino-2-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)acetic acid hydrochloride

HRID 2399636Notes

Reaction equation

HRID 2399636 reaction equation
[N:1]([C@H:4]([CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[C:5]([OH:7])=[O:6])=[N+]=[N-].[ClH:23].[H][H]>O1CCCC1.O.[Pd]>[ClH:23].[NH2:1][CH:4]([CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 15290764HCID 15290764, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 678056032-Amino-2-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)acetic acid hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-α-azido-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid (3.5 g, 1.9 mmol) in tetrahydrofuran (75 mL), water (10 mL), and concentrated hydrochloric acid (1 mL) is added palladium on carbon (0.5 g, 20%). The mixture is shaken under 52 pounds per square inch (psi) of hydrogen at 25° C. for 6 hours. Solid is filtered. The filtrate is concentrated in vacuo to give a light green solid, which is recrystallized in 3N hydrochloric acid (with activated charcoal) to give the title compound as a white solid, 2.84 g; mp 313°-314° C. (dec), [α]D =-47.6° (c=1.0, methanol).

Workup

  1. filtrationSolid is filtered
  2. concentrationThe filtrate is concentrated in vacuo
  3. customto give a light green solid, which
  4. customis recrystallized in 3N hydrochloric acid (with activated charcoal)

Sources & evidence

ORD record
ord-ea5bf77b33e249778b0abbf6a1a3b033
Source dataset
uspto-grants-1995_09
Patent number
US05449778

Reaction notes

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