Hydrochloric Acid → HCID 86673825, compound

HRID 1527344Notes

Reaction equation

HRID 1527344 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][OH:14])[CH2:11][CH2:10][C@H:9]1[C:15](=[O:28])[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[S:36](Cl)([CH3:39])(=[O:38])=[O:37].Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@H:9]([C:15](=[O:28])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:25])([F:26])[F:27])[CH:18]=2)[CH2:10][CH2:11][C@@H:12]1[CH2:13][O:14][S:36]([CH3:39])(=[O:38])=[O:37])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68283314HCID 68283314, compound

Product 1

HCID 86673825HCID 86673825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S,5R)-5-hydroxymethyl-2-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (390 mg, 0.97 mmol) in CH2Cl2 (3.5 mL) was added at 0° C. under nitrogen atmosphere Et3N (296 μl, 2.12 mmol) and mesylchloride (167 μl, 2.12 mmol) and the mixture was further stirred at RT for 3 h. CH2Cl2 and HCl 0.1N were added, the layers were separated and the aqueous one re-extracted with CH2Cl2. The crude organic extracts were washed with brine dried over Na2SO4, filtered and concentrated. The crude material was used without purification in the next step. MS (LC-MS): 383 [MH−Boc]+; tR (HPLC conditions b) 5.1 min.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous one re-extracted with CH2Cl2
  3. washThe crude organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was used without purification in the next step
  8. customtR (HPLC conditions b) 5.1 min.

Sources & evidence

ORD record
ord-e018cf41085542b7bc9cce92d3a6718d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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