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

HRID 1668562Notes

Reaction equation

HRID 1668562 reaction equation
[NH2:1][C:2]1[C:19]([OH:20])=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[C:21](OC)(OC)(OC)[CH3:22].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CN(C=O)C>[CH3:21][C:22]1[O:20][C:19]2[C:2]([N:1]=1)=[CH:3][C:4]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=1[CH:18]=2

Participants

5

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 591504721,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 591504881,1-Dimethylethyl 2-methyl-5,6,8,9-tetrahydro-7H-[1,3]oxazolo[4,5-h][3]benzazepine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (1.7 g) and trimethyl orthoacetate (1.2 ml) in the presence of pyridinium para-toluenesulfonate (0.16 g) were heated in dry DMF (20 ml) for 90 min at 70° C. followed by 2 h at 105° C. Volatiles were evaporated under reduced pressure to give the title compound which was used without further purification.

Workup

  1. customVolatiles were evaporated under reduced pressure

Sources & evidence

ORD record
ord-e49073287e0845efa6d30c06f0564c71
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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