Dimethylformamide → tert-Butyl (S)-(3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl)carbamate

HRID 11599Notes

Reaction equation

HRID 11599 reaction equation
[C:1]([O:5][C:6]([N:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1CN)[C@H](C(O)=O)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)C=[O:25].ON1C2N=CC=CC=2N=N1.Cl.CN(C)[CH2:40][CH2:41][CH2:42][N:43]=[C:44]=NCC>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:14]1[CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:40][C:41]=2[CH2:42][NH:43][C:44]1=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69197459(S)-N-t-butyloxycarbonyl(2-aminomethylphenyl)alanine

Product 1

HCID 69195282tert-Butyl (S)-(3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)—N-t-butyloxycarbonyl(2-aminomethylphenyl)alanine (353 mg), N,N-dimethylformamide (10 mL), dichloromethane (50 mL), 1-hydroxy-7-azabenzotriazole (252 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (180 mg) was stirred at room temperature for 1 h. The solvent was removed under vacuum and the residue was dissolved ethyl acetate (100 mL). This solution was washed sequentially with 1.0 M aqueous hydrochloric acid (50 mL twice), 1.0 M aqueous sodium hydroxide (50 mL), water (50 mL), and brine (50 mL), dried over anhydrous sodium sulfate, and evaporated under vacuum to obtain (S)-4-(t-butyloxycarbonylamino)-2,3,4,5-tetrahydro-2-benzazepin-3(1H)-one (315 mg).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved ethyl acetate (100 mL)
  3. washThis solution was washed sequentially with 1.0 M aqueous hydrochloric acid (50 mL twice), 1.0 M aqueous sodium hydroxide (50 mL), water (50 mL), and brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-ca029937102741169ab21ba3db64bf5e
Source dataset
uspto-grants-2006_08
Patent number
US07098235B2

Reaction notes

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