Methanol → HCID 10151115, compound

HRID 1244710Notes

Reaction equation

HRID 1244710 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H:10]1[NH:18][C:19]([C:21]1[NH:25][C:24]2[C:26]([Cl:30])=[C:27]([Cl:29])[S:28][C:23]=2[CH:22]=1)=[O:20])=[O:7])(=O)C.CO.C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[Cl:29][C:27]1[S:28][C:23]2[CH:22]=[C:21]([C:19]([NH:18][C@@H:10]3[CH2:11][C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C@H:9]3[NH:8][C:6](=[O:7])[CH2:5][OH:4])=[O:20])[NH:25][C:24]=2[C:26]=1[Cl:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 10238658HCID 10238658, compound

Product 1

HCID 10151115HCID 10151115, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{(1R,2R)-1-[(2-Acetoxyacetyl)amino]-2,3-dihydro-1H-inden-2-yl}-2,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxamide (Example 6; 632 mg, 1.36 mmol) was dissolved in THF (10 mL), MeOH (10 mL) and K2CO3 (100 mg) were then added and the suspension stirred at ambient temperature for 16 hours. Water (50 mL) was added and the aqueous phase was extracted with EtOAc (3×30 mL). The combined organic phases were washed with water (2×50 mL), brine (50 mL) and dried (MgSO4). The solvent was removed by evaporation under reduced pressure, the crude product was triturated (EtOAc:isohexane, 1:10), filtered, washed with isohexane (5 mL) and dried to give the title compound (428 mg, 74%) as a white solid.

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (3×30 mL)
  2. washThe combined organic phases were washed with water (2×50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customthe crude product was triturated (EtOAc:isohexane, 1:10)
  6. filtrationfiltered
  7. washwashed with isohexane (5 mL)
  8. customdried

Sources & evidence

ORD record
ord-29b03ad9ed6f4752bc83f8077b3cc7da
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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