Methanol--water (1/1) → HCID 57320683, compound

HRID 751459Notes

Reaction equation

HRID 751459 reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:19][CH2:18][CH2:17][CH:16]([NH:20][C:21](=[O:39])[C@@H:22]([NH:27][C:28]([C:30]2[O:31][C:32]3[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=3[CH:34]=2)=[O:29])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH:15]([OH:40])[CH2:14]1)(=[O:12])=[O:11].CO.O>>[O:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[CH:34]=[C:30]1[C:28]([NH:27][C@@H:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:21]([NH:20][CH:16]1[CH2:17][CH2:18][CH2:19][N:13]([S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:41])=[O:2])(=[O:11])=[O:12])[CH2:14][CH:15]1[OH:40])=[O:39])=[O:29]

Participants

3

Reactant 2

HCID 22242641Methanol--water (1/1)HCID 53969584HCID 53969584, compound2×

Product 1

HCID 57320683HCID 57320683, compoundYield 27.2%

Procedure

2-(4-{(S)-2-[(benzofuran-2-carbonyl)-amino]-4-methyl-pentanoylamino}-3-hydroxy-azepane-1-sulfonyl)-benzoic acid methyl ester (compound 83a, 180 mg, 0.309 mmol) was dissolved in 5:1 MeOH/water (6 ml) LiOH (14 mg, 0.34 mmol) was added and the reaction mixture was stirred and refluxed for 6 h. The reaction mixture was then quenched with water and 6 N HCl (adjusted to pH=2), extracted with EtOAc (3×10 ml), dried with MgSO4, filtered, concentrated, and chromatographed (silica gel, 1% acetic acid/4% MeOH/CH2Cl2) to yield the title compound as a white solid (48 mg, 27%): M+H+=572.2

Workup

  1. additionwas added
  2. temperaturerefluxed for 6 h
  3. customThe reaction mixture was then quenched with water and 6 N HCl (adjusted to pH=2)
  4. extractionextracted with EtOAc (3×10 ml)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (silica gel, 1% acetic acid/4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f564f819901743b7b7796c79ab6fa7ef
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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