Hydrochloric Acid → HCID 140461950, compound

HRID 478971Notes

Reaction equation

HRID 478971 reaction equation
C([O:3][C:4](=[O:41])[CH:5]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[NH:32])=[CH:27][CH:26]=1)[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[C:8]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[C:7]=1[F:23])C.[Na].Cl>C(O)C>[C:37]([O:36][C:34]([NH:33][C:31](=[NH:32])[C:28]1[CH:29]=[CH:30][C:25]([NH:24][CH:5]([C:6]2[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[C:8]([O:15][CH:16]3[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]3)[C:7]=2[F:23])[C:4]([OH:41])=[O:3])=[CH:26][CH:27]=1)=[O:35])([CH3:39])([CH3:38])[CH3:40]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 140461951HCID 140461951, compound

Product 1

HCID 140461950HCID 140461950, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.3 g (RS)-[4-(tert-butoxycarbonylamino-imino-methyl)-phenylamino]-[5-ethoxy-2-fluoro-3-(1-methyl-piperidin-4-yloxy)-phenyl]-acetic acid ethyl ester in 23 ml ethanol was treated with 6.06 ml 1N sodium hydroxyde solution. After one hour, 2.6 ml 1N hydrochloric acid were added until pH=8. The solvent was evaporated and the residue dried to constant weight. It was dissolved in absolute ethanol, filtered, the solution evaporated in vacuo, the residue dried and triturated in ether to yield 2.3 g of (RS)-[4-(tert-butoxycarbonylamino-imino-methyl)-phenylamino]-[5-ethoxy-2-fluoro-3-(1-methyl-piperidin-4-yloxy)-phenyl]-acetic acid.off-white solid. MS: 545 ([M+H]+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue dried to constant weight
  3. dissolutionIt was dissolved in absolute ethanol
  4. filtrationfiltered
  5. customthe solution evaporated in vacuo
  6. customthe residue dried
  7. customtriturated in ether

Sources & evidence

ORD record
ord-9581f7644e514c04bfe7f65cc34c69ae
Source dataset
uspto-grants-2003_11
Patent number
US06642386B2

Reaction notes

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