Lithium Hydroxide → tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamate

HRID 521395Notes

Reaction equation

HRID 521395 reaction equation
[Li+].[OH-].[N+](C1C=CC(C([O:12][C@H:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([C:22]4[CH:47]=[CH:46][C:25]5[C:26]([CH:29]([C:39]6[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=6)[CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[N:27][S:28][C:24]=5[CH:23]=4)[C:16]=3[C@H:15]([CH3:48])[CH2:14]2)=O)=CC=1)([O-])=O>C1COCC1>[Cl:45][C:42]1[CH:41]=[CH:40][C:39]([CH:29]([C:26]2[C:25]3[CH:46]=[CH:47][C:22]([C:21]4[C:16]5[C@H:15]([CH3:48])[CH2:14][C@@H:13]([OH:12])[C:17]=5[N:18]=[CH:19][N:20]=4)=[CH:23][C:24]=3[S:28][N:27]=2)[CH2:30][NH:31][C:32](=[O:33])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67437737HCID 67437737, compound

Product 1

HCID 67438914tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1N LiOH aqueous solution (0.30 mL, 0.30 mmol) was added to a stirred solution of (5R,7R)-4-(3-(2-(tert-butoxycarbonylamino)-1-(4-chlorophenyl)ethyl)benzo[d]isothiazol-6-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (102 mg, 0.149 mmol) in THF (3 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The resulting residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The resulting residue was purified by column chromatography (DCM:MeOH, 60:1) to give tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamate (62 mg, 78%) as an oil. LCMS (APCI+) m/z 537, 539 [M+H]+; Rt=3.99 min.

Workup

  1. customThe solvent was evaporated
  2. customThe resulting residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography (DCM:MeOH, 60:1)

Sources & evidence

ORD record
ord-d5c3e4db8cb84a3fb5e576d59073f00a
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

Loading…