Dimethylformamide → HCID 131736354, compound

HRID 1055429Notes

Reaction equation

HRID 1055429 reaction equation
[H-].[Na+].O=C1C(NC(=O)[C@@H]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])C)C)CSC2C=CC=CC=2N1.C(Br)C1C=CC=CC=1.CN(C=[O:41])C>Cl>[O:41]=[CH:21][CH:18]([O:17][C:16](=[O:22])[NH:15][CH3:23])[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 90060615HCID 90060615, compound

Product 1

HCID 131736354HCID 131736354, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

NaH (60% in mineral oil, 16 mg, 0.40 mmol, Eq: 1.50) was added to a solution of tert-butyl (S)-1-(4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (100 mg, 0.26 mmol, Eq: 1.00) in DMF at RT. After 5 min. benzyl bromide (35 μL, 0.29 mmol, Eq: 1.10) was added, the mixture was stirred for 35 min., diluted with 1 N HCl and extracted with EtOAc. The organic extracts were washed with sat. NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography to afford tert-butyl (S)-1-(5-benzyl-4-oxo-2,3,4,5-tetrahydro-benzo[1)][1,4]thiazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (96 mg, 77%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with sat. NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f5a4a25b86354cef9b87fc18024bc2bc
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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