(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid → 4-[2-(2-Isopropylamino-thiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

HRID 643828Notes

Reaction equation

HRID 643828 reaction equation
[C:1]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C)([O-])C.[K+].[CH:23]([NH:26][C:27]1[S:28][CH:29]=[C:30]([C:32]2[CH:41]=[C:40](O)[C:39]3[C:34](=[CH:35][C:36]([O:43][CH3:44])=[CH:37][CH:38]=3)[N:33]=2)[N:31]=1)([CH3:25])[CH3:24]>CS(C)=O.O>[C:4]([O:3][C:1]([N:8]1[CH2:15][CH:14]([O:16][C:40]2[C:39]3[C:34](=[CH:35][C:36]([O:43][CH3:44])=[CH:37][CH:38]=3)[N:33]=[C:32]([C:30]3[N:31]=[C:27]([NH:26][CH:23]([CH3:25])[CH3:24])[S:28][CH:29]=3)[CH:41]=2)[CH2:13][CH:9]1[C:10]([OH:12])=[O:11])=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 23665647Potassium tert-butoxideHCID 178487686HCID 178487686, compound

Product 1

HCID 749555114-[2-(2-Isopropylamino-thiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of N-Boc-trans-4-hydroxy-L-proline (221 mg, 0.96 mmol) in DMSO was added potassium tert-butoxide (320 mg, 2.9 mmol). After 1 h compound 12 (319 mg, 0.96 mmol) was added and the mixture was stirred at 70° C. for 72 hours. The mixture was diluted with water and extracted with ethyl acetate. The product was used without further purification. Yield 429 mg, 85%.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe product was used without further purification

Sources & evidence

ORD record
ord-b1d75f5cd2874471947e1f34efabce7d
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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