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

HRID 655747Notes

Reaction equation

HRID 655747 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[S:18][C:19]([C:28]([O:30]C)=[O:29])=[C:20]([C:22]4[N:26]([CH3:27])[N:25]=[CH:24][N:23]=4)[N:21]=3)[CH2:13][C@@H:12]2[O:32][CH2:33][CH2:34][CH3:35])=[O:9])[NH:5][C:6]=1[CH3:7].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][C@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[S:18][C:19]([C:28]([OH:30])=[O:29])=[C:20]([C:22]4[N:26]([CH3:27])[N:25]=[CH:24][N:23]=4)[N:21]=3)[CH2:13][C@H:12]2[O:32][CH2:33][CH2:34][CH3:35])=[O:9])[NH:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59402555methyl 2-[(3S,4R)-4-{[(4-chloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-propoxypiperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 667077032-[(3R,4S)-4-{[(4-chloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-propoxypiperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylic acidYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-[(3S,4R)-4-{[(4-chloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-propoxypiperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate (Example 196, 80 mg, 0.153 mmol) was dissolved in methanol (30 mL), and 2N sodium hydroxide (6 mL) was added and stirred at room temperature for 4 h. The methanol was completely evaporated and water (20 mL) was added. The aqueous layer was washed with diethyl ether (2×20 mL) and the aqueous layer was acidified to pH 3 with 2N hydrochloric acid (2.0 mL). The obtained solid was filtered and dried to afford 2-[(3R,4S)-4-{[(4-chloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-propoxypiperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylic acid 60 mg (75%) as solid.

Workup

  1. customThe methanol was completely evaporated
  2. additionwater (20 mL) was added
  3. washThe aqueous layer was washed with diethyl ether (2×20 mL)
  4. filtrationThe obtained solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-358b0ac910464d388bd81776298d593f
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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