Hydrochloric Acid → HCID 20642296, compound

HRID 323371Notes

Reaction equation

HRID 323371 reaction equation
[Li].[C:2]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:50]=[CH:49][C:48]([N:51]2[CH:55]=[N:54][N:53]=[N:52]2)=[CH:47][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][C:15]([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH:29]([NH:32][C:33]3[N:37]([CH2:38][CH2:39][O:40][CH2:41][CH3:42])[C:36]4[CH:43]=[CH:44][CH:45]=[CH:46][C:35]=4[N:34]=3)[CH2:28][CH2:27]2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14]1)=[O:12])([OH:4])=[O:3].Cl.O1CCOCC1>ClCCl>[C:2]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:50]=[CH:49][C:48]([N:51]2[CH:55]=[N:54][N:53]=[N:52]2)=[CH:47][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][C:15]([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH:29]([NH:32][C:33]3[N:37]([CH2:38][CH2:39][O:40][CH2:41][CH3:42])[C:36]4[CH:43]=[CH:44][CH:45]=[CH:46][C:35]=4[N:34]=3)[CH2:28][CH2:27]2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:14]1)=[O:12])([OH:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69955246HCID 69955246, compound

Product 1

HCID 20642296HCID 20642296, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 1-(2-(3-carboxypropyloxy)-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine lithium salt (0.24 mmol) and dichloromethane (5 mL). Add a solution of hydrochloric acid in dioxane (0.18 mL, 4 M, 0.72 mmol). Add methanol (5 mL) and evaporate in vacuo to give a residue. Partition the residue between a saturated aqueous sodium bicarbonate solution and ethyl acetate. Separate the organic layer and extract with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. customAdd methanol (5 mL) and evaporate in vacuo
  2. customto give a residue
  3. customPartition the residue between a saturated aqueous sodium bicarbonate solution and ethyl acetate
  4. customSeparate the organic layer
  5. extractionextract with a saturated aqueous sodium bicarbonate solution
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-6188475efdbb4045867ae7d29ffbeb08
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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