Hydrochloric Acid → HCID 57829572, compound

HRID 1964847Notes

Reaction equation

HRID 1964847 reaction equation
C(OC([NH:8][C@H:9]([C:13]([O:15][CH2:16][CH2:17][C@@H:18]([C:43]1[C:48]([F:49])=[CH:47][CH:46]=[CH:45][C:44]=1[F:50])[NH:19][C:20]([C@H:22]1[N:26]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[F:42])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH2:25][CH2:24][S:23]1)=[O:21])=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.Cl.CS(O)(=O)=O>C(Cl)Cl.O1CCOCC1.C1COCC1>[NH2:8][C@H:9]([C:13]([O:15][CH2:16][CH2:17][C@@H:18]([C:43]1[C:44]([F:50])=[CH:45][CH:46]=[CH:47][C:48]=1[F:49])[NH:19][C:20]([C@H:22]1[N:26]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[F:42])=[CH:32][CH:31]=2)(=[O:28])=[O:29])[CH2:25][CH2:24][S:23]1)=[O:21])=[O:14])[CH:10]([CH3:12])[CH3:11]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 68621532HCID 68621532, compound

Product 1

HCID 57829572HCID 57829572, compoundYield 96.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound (3S)-3-(2,6-difluorophenyl)-3-[({(2S)-3-[(2′-fluorobiphenyl-4-yl)sulfonyl]-1,3-thiazolidin-2-yl}carbonyl)amino]propyl N-(tert-butoxycarbonyl)-L-valinate (3.04 g, 4.13 mmol) was dissolved in DCM (33 mL) at 0 degree and 66 mL of 4M HCl in dioxane was added. The reaction was stirred at 0 degree for 1 h and at r.t. for 3 h. The solvent was evaporated and the residue redissolved in DCM and washed with 10% NaHCO3 and brine. The organic layer was dried over MgSO4 and evaporated to give a white foam. The foam was redissolved in THF and 1 eq of methanesulfonic acid (345 mg) was added, the precipitate was filtered and dried to give the desired product (3S)-3-(2,6-difluorophenyl)-3-[({(2S)-3-[(2′-fluorobiphenyl-4-yl)sulfonyl]-1,3-thiazolidin-2-yl}carbonyl)amino]propyl L-valinate as a white solid (2.53 g, 83.7% yield).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue redissolved in DCM
  3. washwashed with 10% NaHCO3 and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated
  6. customto give a white foam
  7. filtrationthe precipitate was filtered
  8. customdried

Sources & evidence

ORD record
ord-2105b8fcd9464428be7a92203ec89fe1
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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