Benzothiazole → HCID 9849642, compound

HRID 1937809Notes

Reaction equation

HRID 1937809 reaction equation
[Li]CCCC.S1C2C=CC=CC=2N=C1.C1(NC([C:24]2[CH:60]=[CH:59][C:27]3[N:28]=[C:29]([C:31](=[O:58])[C@@H:32]([NH:41][C:42](=[O:57])[C@@H:43]([NH:48][C:49]([N:51]4[CH2:56][CH2:55][O:54][CH2:53][CH2:52]4)=[O:50])[CH2:44][CH:45]([CH3:47])[CH3:46])[CH2:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[S:30][C:26]=3[CH:25]=2)=O)C=CC=CC=1>C1COCC1>[S:30]1[C:26]2[CH:25]=[CH:24][CH:60]=[CH:59][C:27]=2[N:28]=[C:29]1[C:31]([C@@H:32]([NH:41][C:42]([C@@H:43]([NH:48][C:49]([N:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1)=[O:50])[CH2:44][CH:45]([CH3:47])[CH3:46])=[O:57])[CH2:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:58]

Participants

5

Reactant 3

HCID 7222BenzothiazoleHCID 9830851HCID 9830851, compoundHCID 178418339Butyllithium

Product 1

HCID 9849642HCID 9849642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Dry THF (1.5 mL), under Ar, was cooled to −78° C. with a dry-ice/acetone bath. n-BuLi (2.0 M in hexanes) (698 μL, 1.40 mmol) was added to reaction flask followed by dropwise addition of freshly distilled benzothiazole (180 mg, 1.40 mmol) as a solution in 0.5 mL of dry THF. The reaction was stirred for 15 min to give a suspension. A solution of N-(t-butoxycarbonyl)-(N′-methyl-N′-methoxy)-L-homophenylalaninamide (300 mg, 0.930 mmol) (prepared as described in Example 3) in 1 mL of dry THF was added all at once via syringe. The reaction was stirred for 5 min at which time TLC showed consumption of the amide. The reaction was quenched by the addition of water and the product extracted with 50 mL of EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to give a residue that was purified by preparative TLC (CH2Cl2) to give the desired ketone as a clear colorless oil.

Workup

  1. customto give a suspension
  2. stirringThe reaction was stirred for 5 min at which time TLC
  3. customconsumption of the amide
  4. customThe reaction was quenched by the addition of water
  5. extractionthe product extracted with 50 mL of EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue that
  10. customwas purified by preparative TLC (CH2Cl2)

Sources & evidence

ORD record
ord-f84d96536cf14e9284853ffafc269383
Source dataset
uspto-grants-2002_05
Patent number
US06395897B1

Reaction notes

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