Trimethyl orthoacetate → 1,1-dimethylethyl 10-bromo-2-methyl-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5-h][3]benzazepine-7-carboxylate

HRID 1668586Notes

Reaction equation

HRID 1668586 reaction equation
[NH2:1][C:2]1[C:3]([OH:21])=[C:4]([Br:20])[C:5]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7][C:6]=2[CH:19]=1.[C:22](OC)(OC)(OC)[CH3:23].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CN(C=O)C>[Br:20][C:4]1[C:5]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[CH2:8][CH2:7][C:6]=2[CH:19]=[C:2]2[N:1]=[C:22]([CH3:23])[O:21][C:3]=12

Participants

5

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 591505231,1-Dimethylethyl 8-amino-6-bromo-7-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 591504831,1-dimethylethyl 10-bromo-2-methyl-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5-h][3]benzazepine-7-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1-Dimethylethyl 8-amino-6-bromo-7-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (1.604 g) was treated with trimethyl orthoacetate (0.856 ml) and pyridinium p-toluenesulfonate (112 mg) in dry DMF (23 ml) at 60° C. for 1.5 hours. Volatiles were evaporated under reduced pressure and the residue was purified on silica gel (ethyl acetate/petroleum ether: 1/6) providing the title compound as white solid (1.553 g, 90% yield).

Workup

  1. customVolatiles were evaporated under reduced pressure
  2. customthe residue was purified on silica gel (ethyl acetate/petroleum ether: 1/6)

Sources & evidence

ORD record
ord-f3ca554f25444f5d83f101d401d4f036
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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