Sodium Hydroxide → (2S,4R)-1-(tert-butoxycarbonyl)-4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid

HRID 1177535Notes

Reaction equation

HRID 1177535 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:26]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:28]([C:38]([O:40]C)=[O:39])[CH2:27]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[OH-].[Na+]>C1COCC1.O>[C:34]([O:33][C:31]([N:29]1[CH2:30][C@@H:26]([C:4]2[CH:5]=[CH:6][C:7]([C:8]3[S:9][C:10]4[C:15]([N:16]=3)=[CH:14][CH:13]=[C:12]([C:17]3([C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH2:19][CH2:18]3)[N:11]=4)=[C:2]([F:1])[CH:3]=2)[CH2:27][C@H:28]1[C:38]([OH:40])=[O:39])=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67111920(2S,4R)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 67112876(2S,4R)-1-(tert-butoxycarbonyl)-4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-1,2-dicarboxylate (0.100 g, 0.17 mmol) in 2 mL THF was added sodium hydroxide (0.70 mL, 0.70 mmol). The yellow cloudy reaction mixture was diluted with 0.7 mL water, and stirred rapidly at ambient temperature. After 6 h, the reaction mixture was quenched with ice and 5 N HCl until slightly acidic. The aq. Layer was extracted with DCM and the combined extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to give (2S,4R)-1-(tert-butoxycarbonyl)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo-[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid as a white solid. MS (ESI) m/z: Calculated: 559.2; Observed: 559.7 (M++1).

Workup

  1. customThe yellow cloudy reaction mixture
  2. customthe reaction mixture was quenched with ice and 5 N HCl until slightly acidic
  3. extractionThe aq. Layer was extracted with DCM
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65cd57269a2d431c8c67ef8c49713b54
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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