Hydrochloric Acid → HCID 59242731, compound

HRID 2427282Notes

Reaction equation

HRID 2427282 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH2:11][N:12]1[C:20]2[CH:19]=[CH:18][C:17]([C:21]#[N:22])=[CH:16][C:15]=2[C:14]2[CH2:23][C@H:24]([NH:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:25][C:13]1=2)=[O:5])C.[Li+].[OH-].Cl>CCO.C1COCC1>[C:21]([C:17]1[CH:18]=[CH:19][C:20]2[N:12]([CH2:11][C:10]3[S:9][CH:8]=[N:7][C:6]=3[C:4]([OH:5])=[O:3])[C:13]3[CH2:25][C@@H:24]([NH:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:23][C:14]=3[C:15]=2[CH:16]=1)#[N:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67253211HCID 67253211, compound

Product 1

HCID 59242731HCID 59242731, compoundYield 109.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treat a mixture of 5-((S)-7-cyano-2-isopropoxycarbonylamino-2,3-dihydro-1H-cyclopenta[b]indol-4-ylmethyl)-thiazole-4-carboxylic acid ethyl ester (3.745 g, 8.28 mmol) in EtOH (100 mL) and THF (40 mL) with 5 M LiOH (8.3 mL, 41.4 mmol) and stir at room temperature for 18 h. Add 5 N HCl (9 mL) bringing pH to 2. Concentrate the reaction mixture by rotavap, extract into EtOAc (3×330 mL), dry organics (MgSO4), filter, and concentrate to give 3.86 g (>100%) of 5-((S)-7-cyano-2-isopropoxycarbonylamino-2,3-dihydro-1H-cyclopenta[b]indol-4-ylmethyl)-thiazole-4-carboxylic acid as a pale yellow solid. LC-ES/MS m/z 425 (M+1), 423 (M−H), TR=2.3 min.

Workup

  1. additionTreat
  2. concentrationConcentrate the reaction mixture by rotavap
  3. extractionextract into EtOAc (3×330 mL), dry organics (MgSO4)
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-a24f20d4208e4d278d75238e3cef211a
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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