Ammonium Chloride → HCID 19787885, compound

HRID 1656538Notes

Reaction equation

HRID 1656538 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]([NH:12][C:13]2[C:18](=[O:19])[N:17]([CH2:20][C:21]([NH:23][CH:24]([CH:37]([CH3:39])[CH3:38])[CH:25]([O:30]C(=O)C(C)(C)C)[C:26]([F:29])([F:28])[F:27])=[O:22])[C:16]([C:40]3[S:41][CH:42]=[CH:43][CH:44]=3)=C[CH:14]=2)=[O:11])[CH:5]=[C:4]([CH3:45])[N:3]=1.O.[OH-].[Li+].[Cl-].[NH4+:50]>O1CCCC1.CO.O>[CH3:45][C:4]1[CH:5]=[C:6]([CH2:8][O:9][C:10]([NH:12][C:13]2[C:18](=[O:19])[N:17]([CH2:20][C:21]([NH:23][CH:24]([CH:37]([CH3:39])[CH3:38])[CH:25]([OH:30])[C:26]([F:28])([F:27])[F:29])=[O:22])[C:16]([C:40]3[S:41][CH:42]=[CH:43][CH:44]=3)=[N:50][CH:14]=2)=[O:11])[CH:7]=[C:2]([CH3:1])[N:3]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 19787862HCID 19787862, compound

Product 1

HCID 19787885HCID 19787885, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[5-(2,6-dimethylpyrid-4-ylmethoxycarbonylamino)-6-oxo-2-(2-thienyl)-1,6-dihydro-1-pyridinyl]-N-(3,3,3-trifluoro-1-isopropyl-2-pivaloyloxypropyl)acetamide (1.44 g) in tetrahydrofuran (10 mL) and methanol (10 mL) was added a solution of lithium hydroxide monohydrate (0.92 g) in water (20 mL). The resulting solution was stirred for 2 h, diluted with saturated ammonium chloride (30 mL), and extracted with ethyl acetate. The ethyl acetate solution was dried and evaporated. The resulting material was chromatographed, eluting with ethyl acetate, to provide the alcohol (0.39 g) as a yellow foam; TLC: Rf =0.24, ethyl acetate; MS: m/z=568(M+1).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate solution was dried
  3. customevaporated
  4. customThe resulting material was chromatographed
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b7cb54d0cf694041b35c16dbd4210565
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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