Hydrochloric Acid → HCID 68074505, compound

HRID 517701Notes

Reaction equation

HRID 517701 reaction equation
[CH3:1][C@H:2]1[N:7]([CH2:8][C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[N:12]=[N:11][N:10]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.Cl.O1CCOCC1>CO>[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[CH2:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)[N:12]=[N:11][N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86691867HCID 86691867, compound2×

Product 1

HCID 68074505HCID 68074505, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl (3R)-3-methyl-4-({1-[3-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-1-piperazinecarboxylate (527 mg, 1.236 mmol, Intermediate 13) in methanol was added 4M hydrogen chloride in 1,4-dioxane (7 mL, 28.0 mmol). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo to give white crystals. The crude product was poured onto a 5 g SCX cartridge, washed with methanol (2 column volumes) and eluted with ammonia in methanol (2 column volumes). The ammonia in methanol fractions were concentrated and dried in vacuo to yield the title compound as a yellow oil (389 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give white crystals
  3. washwashed with methanol (2 column volumes)
  4. washeluted with ammonia in methanol (2 column volumes)
  5. concentrationThe ammonia in methanol fractions were concentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-621b742966bb4c59b48f40f0c89313b7
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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