Sodium Hydroxide → HCID 58748278, compound

HRID 1162720Notes

Reaction equation

HRID 1162720 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][O:6][C@@H:7]1[C@@H:11]([NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[CH2:10][N:9]([CH2:21][C:22](=[O:38])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]3=[O:36])=[CH:26][C:25]=2[F:37])[CH2:8]1)C.[OH-].[Na+]>C1COCC1>[Cl:20][C:17]1[S:16][C:15]([C:13]([NH:12][C@H:11]2[CH2:10][N:9]([CH2:21][C:22](=[O:38])[NH:23][C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]4=[O:36])=[CH:26][C:25]=3[F:37])[CH2:8][C@@H:7]2[O:6][CH2:5][C:4]([OH:39])=[O:3])=[O:14])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58748267HCID 58748267, compound

Product 1

HCID 58748278HCID 58748278, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 359 mg ((3S,4S)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-1-{[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidin-3-yloxy)-acetic acid ethyl ester (example 96.2) in 10 ml THF was treated with 1.24 ml 1N NaOH and stirred for 5 hrs at r.t. The reaction mixture was concentrated. The crude product was purified by chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 7:3) to give 279 mg ((3S,4S)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-1-{[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidin-3-yloxy)-acetic acid as white solid. MS 549.3 ([M+H]+)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe crude product was purified by chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 7:3)

Sources & evidence

ORD record
ord-05e0674d3a89492b934d9340013581da
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

Loading…