Benzoyl chloride → (S)-(5-Benzoyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester

HRID 1374555Notes

Reaction equation

HRID 1374555 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[N:10]([C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 57617767(S)-tert-Butyl (1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)carbamate

Product 1

HCID 69508172(S)-(5-Benzoyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-(1-Methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester (260 mg, 0.55 mmol), triethylamine (111 mg, 1.1 mmol), and benzoyl chloride (93 mg, 0.66 mmol) were dissolved in dichloromethane (2 ml) and stirred overnight. The reaction mixture was then poured on HCl (1N), and extracted with dichloromethane. The organic layer was washed with NaHCO3 (1N), dried, and evaporated. (S)-(5-Benzoyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester was obtained in sufficient purity for the next step.

Workup

  1. additionThe reaction mixture was then poured on HCl (1N)
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with NaHCO3 (1N)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-a71a1d4fc5954837b76049576ba30331
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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