Hydrochloric Acid → HCID 10141903, compound

HRID 1358143Notes

Reaction equation

HRID 1358143 reaction equation
[F:1][CH:2]([F:37])[O:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6]1[CH:31]=[CH:30][C:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][C:7]=1[CH:8]([C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[CH:17]=[CH:18][CH:19]=1)[O:9]2.[Li+].[OH-].Cl>CO>[F:37][CH:2]([F:1])[O:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6]1[CH:31]=[CH:30][C:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][C:7]=1[CH:8]([C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:17]=[CH:18][CH:19]=1)[O:9]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10302050HCID 10302050, compound

Product 1

HCID 10141903HCID 10141903, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 115 (110 mg, 0.21 mmol) and aqueous LiOH (1 ml of 10% solution) in methanol (1 ml) was stirred for 3 hours, neutralized with 1M HCl, and extracted with ethyl acetate. The extract was dried (MgSO4) and concentrated. The concentrate was purified by high throughput HPLC with aqueous 0.1% TFA and CH3CN to provide the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 8.15 (d, J=9 Hz, 1H) 6.87-7.56 (m, 10H), 6.24 (s, 1H), 3.00 (s, 1H), 2.55 (t, J=7 Hz, 2H), 2.17 (t, J=7 Hz, 2H), 1.73 (m, J=7 Hz, 2H); MS (ESI(−)Q1MS m/z 502 (M−H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe concentrate was purified by high throughput HPLC with aqueous 0.1% TFA and CH3CN

Sources & evidence

ORD record
ord-3616ae7976c949beba53e4df821b56e8
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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