Hydrochloric Acid → HCID 86755669, compound

HRID 1872457Notes

Reaction equation

HRID 1872457 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([OH:25])[C@@:10]2([N:22]=[N+:23]=[N-:24])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:5])[CH3:2].[C:26](C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.O(C)S(C(F)(F)F)(=O)=O.Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([O:25][CH3:26])[C@@:10]2([N:22]=[N+:23]=[N-:24])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9526Methyl triflateHCID 685102,6-Di-tert-butylpyridineHCID 11772339HCID 11772339, compound

Product 1

HCID 86755669HCID 86755669, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (VII-1) (345 mg, 1.0 mmol), 2,6-di-tert.-butylpyridine (1.35 mL, 6.0 mmol) and methyl triflate (0.55 mL, 5.0 mmol) in DCM (2 mL) was stirred at 23° C. for 4 d. The reaction mixture was poured on ice, acidified with 1 N HCl and extracted with ether. After washing with sat. NaHCO3 -sol., brine and drying over MgSO4 the crude product was purified by silica gel column chromatography with hexane/EtOAc 4:1 to give (1S,2R,3R,5R,6S)-2-azido-3-methoxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXIII-1) (226 mg, 63%) as a yellow oil. 1H-NMR (250 MHz, CDC13) □1.26 (3H, t, J=7.1 Hz), 1.77 (1H, t, J=3.5 Hz), 2.05-2.18 (2H, m), 2.25 (1H, dd, J=7, 3.5 Hz), 2.34 (1H, dd, J=12, 7 Hz), 3.28 (3H, s), 3.42 (1H, bt,J=8 Hz), 4.12 (2H, q, J=7.1 Hz), 5.25 (1H, d,J=12 Hz), 5.34 (1H, d, J=12 Hz), 7.30-7.40 (5H, m); MS [EI] 258 [ (M--CO2Et-N2)+ ]; □D20 -48.02° (c=1.11, CHCl3).

Workup

  1. additionThe reaction mixture was poured on ice
  2. extractionextracted with ether
  3. washAfter washing with sat. NaHCO3 -sol
  4. dry with material, brine and drying over MgSO4 the crude product
  5. customwas purified by silica gel column chromatography with hexane/EtOAc 4:1

Sources & evidence

ORD record
ord-3c4d9073f84042148fb067a39e6aa6c6
Source dataset
uspto-grants-2000_08
Patent number
US06107342

Reaction notes

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