Hydrochloric Acid → HCID 58748169, compound

HRID 1162622Notes

Reaction equation

HRID 1162622 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([NH:10][C:11]([C:13]2[S:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[O:12])[CH2:7][N:6]1[CH2:19][C:20](=[O:36])[NH:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]2=[O:34])=[CH:24][C:23]=1[F:35])=[O:4].[OH-].[Na+].Cl>C1COCC1>[Cl:18][C:15]1[S:14][C:13]([C:11]([NH:10][C@H:8]2[CH2:7][N:6]([CH2:19][C:20](=[O:36])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]4=[O:34])=[CH:24][C:23]=3[F:35])[C@H:5]([C:3]([OH:4])=[O:2])[CH2:9]2)=[O:12])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 42643337HCID 42643337, compound

Product 1

HCID 58748169HCID 58748169, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 394 mg (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-1-{[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidine-2-carboxylic acid methyl ester (example 11.4) in 10 ml THF was treated with 1.5 ml 1N NaOH. The reaction mixture was stirred for 4 hrs at r.t., then brought to pH 7 with 3N HCl and concentrated. The crude product was purified by chromatography (silica gel; CH2Cl2/MeOH 4:1, then MeOH). The product-containing fractions were concentrated, triturated with water and dried to give 290 mg (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-1-{[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidine-2-carboxylic acid as an off-white solid. MS 519.3 ([M+H]+)

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by chromatography (silica gel
  3. concentrationThe product-containing fractions were concentrated
  4. customtriturated with water
  5. customdried

Sources & evidence

ORD record
ord-357d9d07309848faa48027a1d9428e8c
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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