Hydrochloric Acid → HCID 53855103, compound

HRID 617317Notes

Reaction equation

HRID 617317 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])=O)(C)(C)C.Cl[C:16]1[CH:17]=[C:18](O)[CH:19]=[N:20][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[ClH:54].C([O-])(O)=O.[Na+]>>[Cl:54][C:19]1[C:18]([O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:17][CH:16]=[CH:21][N:20]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 5823053-Hydroxy-5-chloropyridineHCID 643448(S)-(-)-N-Boc-prolinolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 53855103HCID 53855103, compound

Procedure

(S)-1-t-Butoxycarbonyl-2-pyrrolidinemethanol (2.01 g, 10.0 mmol, prepared in Example 15a) and 5chloro-3-pyridinol (1.454 g, 11.0 mmol, Aldrich Chemical Co.). were allowed to react in the presence of triphenylphosphine and DEAD as described in Example 2a. The crude product was hydrolyzed with 10% HCl at room temperature for 0.5 hours. The solution was made basic with NaHCO3, then extracted with ethyl acetate. After removal of the solvent, the residue was purified by chromatography over silica gel to give 166.5 mg of the title product. MS (DCI/NH3) m/e: 213 (M+H)+ and 215 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 7.99 (d, J=5.1 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 7.20 (dd, J=5.1, 8.5 Hz), 1H), 4.08-4.01 (m, 1H), 4.40-3.94 (m, 1H), 3.69-3.58 (m, 1H), 3.15-2.98 (m, 2H), 2.07-1.61 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter removal of the solvent
  3. customthe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-39604ab432ca49e58ba54c9e2ccbad8c
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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