Tetrahydrofuran → HCID 59174865, compound

HRID 1177643Notes

Reaction equation

HRID 1177643 reaction equation
C([O:4][C@@H:5]([CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][C:21]3[C:26]([N:27]=2)=[CH:25][CH:24]=[C:23]([C:28]2([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:30][CH2:29]2)[N:22]=3)=[C:15]([F:37])[CH:14]=1)=[O:11])[C:6]([OH:8])=[O:7])(=O)C.C1COCC1.[OH-].[Na+]>>[F:37][C:15]1[CH:14]=[C:13]([NH:12][C:10](=[O:11])[CH2:9][C@H:5]([OH:4])[C:6]([OH:8])=[O:7])[CH:18]=[CH:17][C:16]=1[C:19]1[S:20][C:21]2[C:26]([N:27]=1)=[CH:25][CH:24]=[C:23]([C:28]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:29][CH2:30]1)[N:22]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67111545HCID 67111545, compound

Product 1

HCID 59174865HCID 59174865, compound

Procedure

(2S)-2-Acetoxy-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)-4-oxobutanoic acid (7.0 mg, 13 μmol) was dissolved in THF (135 μl, 13 μmol) before 0.1 N sodium hydroxide (404 μl, 40 μmol) was added and stirred at ambient temperature for 24 h. The reaction mixture was concentrated to give (2S)-4-((3-fluoro-4-(5-(1-phenylcyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)phenyl)amino)-2-hydroxy-4-oxobutanoic acid after preparative LC purification. MS (ESI) m/z: Calculated: 476.1; Observed: 477.7 (M++H).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a45842b25ee3453caff18d34b0c74da0
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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