Hydrochloric Acid → HCID 11490920, compound

HRID 902783Notes

Reaction equation

HRID 902783 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:53])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([CH2:26][C:27]2[N:28]=[C:29]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([NH:40][CH2:41][C:42]4[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[CH:44][CH:43]=4)=[O:39])=[CH:34][CH:33]=3)[S:30][CH:31]=2)[C:16](=[O:25])/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][CH:9]=1.Cl>CO>[CH2:48]([C:45]1[CH:44]=[CH:43][C:42]([CH2:41][NH:40][C:38]([C:35]2[CH:34]=[CH:33][C:32]([C:29]3[S:30][CH:31]=[C:27]([CH2:26][N:15]([CH2:14][C:11]4[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]([OH:53])=[O:4])=[CH:9][CH:10]=4)[C:16](=[O:25])/[CH:17]=[CH:18]/[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:28]=3)=[CH:37][CH:36]=2)=[O:39])=[CH:47][CH:46]=1)[CH2:49][CH2:50][CH2:51][CH3:52]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58693679HCID 58693679, compound

Product 1

HCID 11490920HCID 11490920, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1N aqueous NaOH (0.5 mL) was added to a solution of methyl[4-({{[2-(4-{[(4-pentylbenzyl)amino]carbonyl}phenyl)-1,3-thiazol-4-yl]methyl}[(2E)-3-phenylprop-2-enoyl]amino}methyl)phenoxy]acetate (163 mg, 0.23 mmol) in MeOH (5 mL). The reaction mixture was stirred at RT for 2 hours, then poured into 1N aqueous HCl (25 mL). The resulting precipitate was filtered, washed with water (3×) and dried under reduced pressure to give 120 mg (75%) of the title compound as a white solid. M+(ESI): 688.1; M−(ESI): 686.5. HPLC, Rt: 5.3 min (purity: 100%). 1H NMR (CDCl3) δ: 7.97-7.79 (m, 5H), 7.50-7.01 (m, 13H), 6.84 (m, 2H), 6.57 (m, 1H), 4.88 (brs, 2H), 4.75 (brs, 2H), 4.60 (m, 4H), 2.60 (t, J=7.7 Hz, 2H), 1.61 (m, 2H), 1.33 (m, 4H), 0.90 (t, J=6.4 Hz, 3H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water (3×)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-20501a7a4eec4ac29e77196043011c62
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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