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

HRID 1372967Notes

Reaction equation

HRID 1372967 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].C(N(C(C)C)C(C)C)C.[C:19]([O:23][C:24](=[O:39])[NH:25][C@@H:26]1[C:32](=[O:33])[N:31]([CH3:34])[C:30]2[CH:35]=[CH:36][CH:37]=[CH:38][C:29]=2[NH:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:19]([O:23][C:24](=[O:39])[NH:25][C@@H:26]1[C:32](=[O:33])[N:31]([CH3:34])[C:30]2[CH:35]=[CH:36][CH:37]=[CH:38][C:29]=2[N:28]([S:2]([CH3:1])(=[O:5])=[O:3])[CH2:27]1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 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 69043284((S)-5-methanesulfonyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 623 mg (3.4 mmol) of methanesulfonic acid anhydride and 0.12 ml (0.7 mmol) of N-ethyl-diisopropylamine was cooled to 0° C. and treated with a solution of 200 mg (0.7 mmol) of (S)-(1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester in 2 ml of dichloromethane. The reaction mixture was left to warm to room temperature and stirred during 18 h. For the working-up, the reaction mixture was cooled to 0° C. and treated with a saturated solution of sodium carbonate. The organic layer was separated, washed with a saturated solution of ammonium hydrochloride and water, finally dried over sodium sulphate and evaporated. For purification, the crude material was chromatographed on silical gel using a 96:4-mixture of dichloromethane and ethyl acetate as the eluent. There were obtained 100 mg (40% of theory) of the ((S)-5-methanesulfonyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester as a white foam;

Workup

  1. waitThe reaction mixture was left
  2. temperatureto warm to room temperature
  3. temperaturethe reaction mixture was cooled to 0° C.
  4. customThe organic layer was separated
  5. washwashed with a saturated solution of ammonium hydrochloride and water
  6. dry with materialfinally dried over sodium sulphate
  7. customevaporated
  8. customFor purification
  9. customthe crude material was chromatographed on silical gel

Sources & evidence

ORD record
ord-1a4e553dba4647eca0874b967866b6f1
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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