Hydrochloric Acid → HCID 66839966, compound

HRID 1509867Notes

Reaction equation

HRID 1509867 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH:5]([NH:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)=[CH:17][CH:16]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8].[ClH:34]>>[ClH:34].[ClH:34].[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH:5]([NH:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:19][CH:20]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 58809795HCID 58809795, compound

Product 1

HCID 66839966HCID 66839966, compoundYield 88%

Procedure

3-{2-[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]ethylamino}pentanedioic acid dimethyl ester (2) (0.57 g, 1.22 mmol) and saturated methanolic HCl were stirred together at ambient temperature for 3 hours. Subsequent evaporation of the solvent followed by further drying under high vacuum for 12 hours afforded the compound 18 (0.47 g, 88% yield) as a viscous oil: 1H NMR (500 MHz, CDCl3) δ 1.46-1.52 (m, 2H), 1.55-1.64 (m, 2H), 2.56-2.58 (m, 4H), 2.64-2.65 (m, 2H), 2.72-2.79 (m, 2H), 2.88-2.93 (m, 2H), 3.74 (d, 6H), 3.88-3.93 (m, 1H), 4.44-4.49 (m, 2H), 6.40 (br, 1H), 6.85 (d, 2H), 7.09 (d, 2H), 8.27 (br, 2H).

Workup

  1. customSubsequent evaporation of the solvent
  2. customby further drying under high vacuum for 12 hours

Sources & evidence

ORD record
ord-2ba106058fc448939c3d5dba079e75d4
Source dataset
uspto-grants-2012_07
Patent number
US08211895B2

Reaction notes

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