Hydrochloric Acid → HCID 58778867, compound

HRID 1372611Notes

Reaction equation

HRID 1372611 reaction equation
Cl.C(O[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17]1)=[O:8])(C)(C)C.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34]1[O:35][C:36]2[CH:42]=[C:41]([CH2:43]C(O)=O)[CH:40]=[CH:39][C:37]=2[N:38]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl.C(Cl)CCl>[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34]1[O:35][C:36]2[CH:42]=[C:41]([CH2:43][C:7]([N:9]3[CH2:13][CH2:12][CH2:11][C@H:10]3[CH2:14][O:15][CH:16]3[CH2:17][CH2:18][CH:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:20][CH2:21]3)=[O:8])[CH:40]=[CH:39][C:37]=2[N:38]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 235083152-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acidHCID 44605973HCID 44605973, compound

Product 1

HCID 58778867HCID 58778867, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (20 ml), EDC(HCl (691 mg, 3.6 mmol) was added at 0° C. to methyl 4-(1-(tert-butoxycarbonyl)-(2S)-pyrrolidinylmethoxy)cyclohexanecarboxylate (580 mg, 2.4 mmol), 2-(2-methylphenylamino)-6-benzoxazolylacetic acid (678 mg, 2.4 mmol), HOBt (324 mg, 2.4 mmol) and triethylamine (1.0 ml, 7.2 mmol). The reaction mixture was stirred at room temperature for 16 hours. Ice water (10 ml) was added and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate, a 2M aqueous citric acid solution and a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (1:2, v/v) eluate fractions, the title compound (500 mg, 48%) was obtained as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala 2M aqueous citric acid solution and a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (1:2, v/v) eluate fractions

Sources & evidence

ORD record
ord-7e6d5b61cda34700a519c09f5a492d0d
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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