Sodium Hydroxide → 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylic acid

HRID 655732Notes

Reaction equation

HRID 655732 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:29]([O:31]C)=[O:30])=[C:21]([C:23]3[N:27]([CH3:28])[N:26]=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:33][CH2:34][CH:35]=[CH2:36])=[O:10].[OH-].[Na+]>CO>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:29]([OH:31])=[O:30])=[C:21]([C:23]3[N:27]([CH3:28])[N:26]=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:33][CH2:34][CH:35]=[CH2:36])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 46234299methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 462359882-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate (Example 30, 90 mg, 0.162 mmol) and 2N sodium hydroxide (4 mL) in methanol (30 mL) was stirred at room temperature for 4 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in water, which was acidified to pH 3 with 2 N hydrochloric acid (2 mL). The resulting solid was collected by filtration and dried to afford 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylic acid (40 mg, 72%) as solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water
  3. filtrationThe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-0b81137b24854d528107d9d45d346b21
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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