Hydrochloric Acid → HCID 178503712, compound

HRID 1879580Notes

Reaction equation

HRID 1879580 reaction equation
[ClH:1].C(OC([NH:9][C@@H:10]([CH2:32][CH2:33][S:34][CH3:35])[C:11]([NH:13][C@@:14]1([C:29]([OH:31])=[O:30])[CH2:19][C@@H:18]([S:20][C:21]2[NH:25][CH:24]=[N:23][N:22]=2)[C@@H:17]2[C@H:15]1[C@H:16]2[C:26]([OH:28])=[O:27])=[O:12])=O)(C)(C)C.COC(C)(C)C>O1CCOCC1>[ClH:1].[NH2:9][C@@H:10]([CH2:32][CH2:33][S:34][CH3:35])[C:11]([NH:13][C@@:14]1([C:29]([OH:31])=[O:30])[CH2:19][C@@H:18]([S:20][C:21]2[NH:25][CH:24]=[N:23][N:22]=2)[C@@H:17]2[C@H:15]1[C@H:16]2[C:26]([OH:28])=[O:27])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 178503713HCID 178503713, compound

Product 1

HCID 178503712HCID 178503712, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Add 4M hydrogen chloride in 1,4-dioxane (19.35 mL, 77.38 mmol) dropwise to a solution of (1R,2S,4R,5R,6R)-2-[[(2S)-2-(tert-butoxycarbonylamino)-4-methylsulfanyl-butanoyl]amino]-4-(4H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (2.66 g, 5.16 mmol) in 1,4-dioxane (26.6 mL) at room temperature in a water bath, and maintain stirring overnight at room temperature. Add methyl-t-butyl ether (200 mL) and stir the mixture for 2 hours. Filter the solid and dry in vacuo overnight. Redissolve the material in water and freeze-dry overnight. Triturate the solid in acetone (10 volumes) at reflux, filter and dry in vacuo under nitrogen for 48 hours to give the title compound (2.33 g, 5.16 mmol) as a white solid. MS (m/z): 416 (M+1).

Workup

  1. temperaturemaintain
  2. filtrationFilter the solid
  3. customdry in vacuo overnight
  4. dissolutionRedissolve the material in water
  5. customfreeze-dry overnight
  6. customTriturate the solid in acetone (10 volumes)
  7. temperatureat reflux
  8. filtrationfilter
  9. customdry in vacuo under nitrogen for 48 hours

Sources & evidence

ORD record
ord-5c57087de4f04fc9a8a826c66c4e424c
Source dataset
uspto-grants-2012_11
Patent number
US08318184B2

Reaction notes

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