Methanol → 3-Methoxysulfonylamino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]butanamide

HRID 1591495Notes

Reaction equation

HRID 1591495 reaction equation
[NH2:1][C@@H:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].C(N(CC)CC)C.Cl[S:22]([N:25]1[C:28]([CH3:30])([CH3:29])[CH2:27][C:26]1=[O:31])(=[O:24])=[O:23].[CH3:32][OH:33]>>[CH3:32][O:33][S:22]([NH:25][C:28]([CH3:30])([CH3:29])[CH2:27][C:26]([NH:1][C@@H:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13])=[O:31])(=[O:24])=[O:23]

Participants

5

Reactant 4

HCID 887Methanol3×HCID 8471TriethylamineHCID 10103689(R)-3-amino-4,5-dihydro-1H-benzo[b]azepin-2(3H)-oneHCID 109434452,2-Dimethyl-4-oxoazetidine-1-sulfonyl chloride

Product 1

HCID 108615583-Methoxysulfonylamino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]butanamide

Conditions

Temperature
0 °C

Procedure

A suspension of 98.31 g (0.530 mol) of 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one in 1600 mL of methanol at room temperature was treated with 155 mL (1.112 mol) of triethylamine. The resulting suspension was cooled to 0° C. and treated with a solution of 110.01 g (0.557 mol) of N-chlorosulfonyl-4,4-dimethylazetidin-2-one in 960 mL of methanol over 20 minutes maintaining the internal temperature below 10° C. Additional methanol (100 mL) was used to rinse the flask and the rinse was transferred into the reaction vessel. The reaction mixture was warmed to room temperature and stirred for 90 minutes.

Workup

  1. temperaturemaintaining the internal temperature below 10° C
  2. washto rinse the flask
  3. temperatureThe reaction mixture was warmed to room temperature

Sources & evidence

ORD record
ord-af771d7d163946a1aaf62632898509db
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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