Hydrochloric Acid → HCID 59788417, compound

HRID 29472Notes

Reaction equation

HRID 29472 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]2[C:12]([CH3:41])=[C:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([S:29]([NH:32][C@H:33]([C:37]([O:39]C)=[O:38])[CH:34]([CH3:36])[CH3:35])(=[O:31])=[O:30])=[CH:25][CH:24]=4)=[CH:19][CH:18]=3)[O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1.[OH-].[Li+].Cl.C(OCC)(=O)C>O1CCCC1.CO.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]2[C:12]([CH3:41])=[C:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([S:29]([NH:32][C@H:33]([C:37]([OH:39])=[O:38])[CH:34]([CH3:36])[CH3:35])(=[O:31])=[O:30])=[CH:25][CH:24]=4)=[CH:19][CH:18]=3)[O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 68716518HCID 68716518, compound

Product 1

HCID 59788417HCID 59788417, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl N-[(4′-{[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methoxy}-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate (192 mg, 0.331 mmol) in tetrahydrofuran (12 mL), methanol (8 mL), water (4 mL) was added lithium hydroxide (317 mg, 13.25 mmol). After stirring for 2.5 days at room temperature hydrochloric acid (13.25 mL, 1 N solution) was added followed by ethyl acetate (80 mL). The layers were separated and the organic phase was washed with water, dried over sodium sulfate, filtered and reduced to dryness. The solid material was recrystallized from a minimum amount of boiling isopropanol to furnish which furnished 171 mg (91%) of N-[(4′-{[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methoxy}-1,1′-biphenyl-4-yl)sulfonyl]-L-valine as a white solid. MS (ES) m/z: 564.2 (M−H), 1129.4 (2M−H).

Workup

  1. additionwas added
  2. customThe layers were separated
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solid material was recrystallized from a minimum amount of boiling isopropanol
  7. customto furnish which

Sources & evidence

ORD record
ord-602841cd313d40798624ee12c7ab7ce4
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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