Trimethyl orthoacetate → HCID 59150518, compound

HRID 1668592Notes

Reaction equation

HRID 1668592 reaction equation
[NH2:1][C:2]1[C:3]([OH:21])=[C:4]([CH3:20])[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>[CH3:22][C:23]1[O:21][C:3]2[C:2]([N:1]=1)=[CH:19][C:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[CH2:10][CH2:11][C:5]=1[C:4]=2[CH3:20]

Participants

5

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67358883HCID 67358883, compound

Product 1

HCID 59150518HCID 59150518, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1-Dimethylethyl 8-amino-7-hydroxy-6-methyl-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (1.1 g) was treated with trimethyl orthoacetate (0.718 ml) and pyridinium p-toluenesulfonate (94 mg) in dry DMF (19 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: 1/4) providing the title compound as white solid (1.127 g, 94% yield).

Workup

  1. customVolatiles were evaporated under reduced pressure
  2. customthe residue was purified on silica gel (ethyl acetate/petroleum ether: 1/4)

Sources & evidence

ORD record
ord-06d78a82c2f2444b9742829b442d28dc
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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