Acetyl chloride → HCID 58742487, compound

HRID 722277Notes

Reaction equation

HRID 722277 reaction equation
CCN(C(C)C)C(C)C.[C:10](Cl)(=[O:12])[CH3:11].[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([C:24]([NH:26][C@@H:27]1[CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C@H:28]1[NH:36][CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:25])=[CH:18]2>C1COCC1>[C:10]([N:36]([CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@@H:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:35][C@H:27]1[NH:26][C:24]([C:19]1[NH:20][C:21]2[C:17]([CH:18]=1)=[CH:16][C:15]([Cl:14])=[CH:23][CH:22]=2)=[O:25])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 58742476HCID 58742476, compound

Product 1

HCID 58742487HCID 58742487, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIPEA (80 μL, 0.5 mmol) and acetyl chloride (30 μL, 0.5 mmol) were added to a solution of 1,1-dimethylethyl [((1R,2R)-2-{[(5-chloro-1H-indol-2-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)amino]acetate (Method 8, 200 mg, 0.5 mmol) in THF (10 mL). The reaction was stirred at ambient temperature for approximately 1 h. The volatiles were removed by evaporation under reduced pressure the residue dissolved in EtOAc (50 mL), washed with water (2×10 mL), brine (10 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure and the residue purified by column chromatography (EtOAc:isohexane 1:1) to afford the title compound (168 mg, 76%) as a white solid.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure the residue
  2. dissolutiondissolved in EtOAc (50 mL)
  3. washwashed with water (2×10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were removed by evaporation under reduced pressure
  6. customthe residue purified by column chromatography (EtOAc:isohexane 1:1)

Sources & evidence

ORD record
ord-db8aff9e9f5c4a0b875fe5a0308481a8
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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