L-Methionine → Benzyl (3R)-6-bromo-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

HRID 501115Notes

Reaction equation

HRID 501115 reaction equation
N[C@H](C(O)=O)CCSC.[Br:10][C:11]1[CH2:17][N:16](CC2C=CC(OC)=CC=2OC)[C:15](=[O:29])[C@H:14]([NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:13][CH:12]=1>FC(F)(F)C(O)=O.ClCCl>[Br:10][C:11]1[CH2:17][NH:16][C:15](=[O:29])[C@H:14]([NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:13][CH:12]=1

Participants

5

Reactant 2

HCID 6137L-MethionineHCID 60037867Benzyl (3R)-6-bromo-1-(2,4-dimethoxybenzyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

Product 1

HCID 23657091Benzyl (3R)-6-bromo-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamateYield 27.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of L-methionine (274 mg, 1.84 mmol) in trifluoroacetic acid (5 mL) was added to a solution of benzyl (3R)-6-bromo-1-(2,4-dimethoxybenzyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (90 mg, 0.184 mmol) in dichloromethane (5 mL). After 18 h, the mixture was concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (17 mg). MS 339 (M+1).

Workup

  1. concentrationthe mixture was concentrated
  2. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-c3a6ca165dd148cd8690c1fd279d9a30
Source dataset
uspto-grants-2010_08
Patent number
US07772224B2

Reaction notes

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